


Wooden Nickels

by Schaden_freude



Category: Bendy and the Ink Machine, Cuphead (Video Game)
Genre: Alternate Universe - 1920s, Alternate Universe - Prohibition Era, Boss/Employee Relationship, Crossover Pairings, Historical References, M/M, Organized Crime, Other Additional Tags to Be Added, POV Alternating, POV First Person, Please Read Chapter Notes for Individual Warnings!, Slow Romance, Some cartoon violence, Various other BATIM characters, Various other Cuphead characters, Various other Disney characters
Language: English
Status: Completed
Published: 2020-10-16
Updated: 2021-01-20
Packaged: 2021-03-09 01:27:51
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 26,266
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27036442
Author URL: https://archiveofourown.org/users/Schaden_freude/pseuds/Schaden_freude
Summary: In Toontown during the Roaring 20s, anything is possible. A working class street rat named Cuphead attracts the attention of Bendy, the local Mafia boss and one of the seven heads of the city's crime syndicate. The unlikely pair is thrown into strange and dangerous adventures, complete with satanic cults, corrupt cops, and terrifying demons. Through it all, Bendy and Cuphead unexpectedly find themselves becoming friends. But will their relationship evolve into something more? Of course it will. It's fanfiction.
Relationships: Bendy (Bendy and the Ink Machine)/Cuphead (Cuphead)
Comments: 29
Kudos: 22





	1. Detective Work

**Author's Note:**

> Don't take any wooden nickels = 1920s slang for 'Don't do anything stupid'
> 
> Chapter Warnings: Cartoon violence

Cuphead’s POV 

Being a hero is sort of like standing on the edge of a cliff. You never know what kind of hero you are until you take that leap, without a thought as to what’s gonna catch you at the bottom. Some people jump off the edge all the time, like they’re on some bungee cord. Others just stay on the edge, too scared to take the risk, too scared to be the hero. Me, when I jumped off my cliff, I was lucky. ‘Cause I had a net. Bendy was my net. Bendy has been my net ever since. 

This isn’t a story about heroes. If anything, it’s a story about bad guys. But eventually, even bad guys have to take that leap. 

My name’s Cuphead, and this is how I made that leap. 

When I was two years old, I was abandoned on a doorstep, desperately clutching my baby brother, Mugman. That’s what Elder Kettle says, anyhow, and he raised us. It was his doorstep we were left on. I was “holding that baby closer than a cat at a mouse hole, and wouldn’t put him down neither,” according to Elder Kettle, and he would know. 

Elder Kettle ran an orphanage, a little brownstone squashed between two big tenement apartments. Awfully strange place for an orphanage, I thought, there in the middle of the big bustling city, but there it was and there was where we grew up. 

It was me and Mugman and ten or twelve other little boys living there, and good old Elder Kettle took care of us. Real nice guy, Elder Kettle. He never beat us or mistreated us or starved us, and he hardly ever yelled if he didn’t have to. And he was a gosh darn angel when it came to patience. And you just had to be patient when dealing with ten or twelve little boys with no parents or discipline or anything. When he did get mad, steam would come pouring out of his spout and he’d have to take a deep breath to relax. 

Good old Elder Kettle taught us our letters too, or as much as we bothered to sit down for, anyway. We just didn’t have much time for learning, nor the inclination, for that matter. Mugman, though, he took to reading like a fish to water. I’ve never seen a boy try to read as much as he did. But more on that later. 

You can probably guess that I wasn’t exactly the perfect child. Elder Kettle said I was “spirited”. Mugman said I was “too rough for my own good”. And the other boys said I was just plain “crazy.” These are all understatements. I was fiendishly adventurous and recklessly stubborn. Something in me was just aching to get out into the world, to jump and run and shout and watch, and hoo boy did it get me in trouble. I used to jump trains and walk the edges of roofs and run from cops and just generally stick my nose where it didn’t belong. I discovered all the hidden nooks and crannies on the street where we lived, and all the fellas at the local police station knew me by name. Seems like just about anything dangerous, or scary, or just plain insane had my name on it. 

I usually ended up dragging Mugman or some of the other boys along on these little adventures of mine. They didn’t always have the same enthusiasm, but Mugman was usually by my side in a pinch. Gosh, but he is a good brother! You’ve never seen a smarter kid. That boy could convince the president to abolish taxes, I swear he was that clever. His quick wit and polite manner surely got us out of many a scrape. When my brawn didn’t work, his brain stepped in. Lord, we were quite the duo back in those days. 

Whenever I got in trouble, which was quite often, Elder Kettle would just glare up at the sky, as though asking God what he’d done to deserve this, and he’d say that one day I was gonna give him a heart attack. I know I scared and hurt Elder Kettle sometimes. And sometimes I was a little rough and shoved Mugman a little too hard, or pushed around one of the boys too much. But I didn’t mean anything by it. Really. It was all just in fun. I ain’t one to shy away from consequences. No sir. I paid my dues, I’ve paid them ten times over. 

I am happy to report that Elder Kettle did indeed survive my childhood, and never had that oft-predicted heart attack. He sure got mad enough that sometimes, in the middle of him yelling at me, I thought he’d keel over and die just out of plain spite. But Elder Kettle was good to us. Yeah. Elder Kettle was real good to us. 

By and by the years passed, and Mug and I were growing up. New kids came to the orphanage, and pretty soon we felt bad about living off of Elder Kettle’s dime. He never asked us to leave, of course. But by the time I was just about getting into manhood, I knew it was time to head out into the wide old world and make something of myself. Mugman came with me, even though he was still a boy. We pooled our savings and Elder Kettle lent us a little money, enough so we could buy a little tenement apartment not too far away. Gosh, but that place was tiny. Practically a closet. Hardly any room for two growing guys to stretch out in. 

Well, that was the end of our adventures. There just wasn’t any time to be jumping or running or shouting or watching, not when there was rent to pay and work to do. Pretty soon most memories of that happier time faded away, replaced by hours and hours at the damn honey factory. That place was a regular slaughterhouse, let me tell you. Day in and day out, me and a bunch of other faceless guys stood stock still and scooped globs of sticky honey into jars, to be sold to the general public at sky high prices. It was boring beyond boring, but if you wanted to get out, another guy was always happy to take your place and then you were on the streets again, wondering where the heck your next meal was coming from. Nah, if you had half a brain you’d keep in your place, even if it was hard to work with Rumor Honeybottoms and her thugs breathing down your neck. 

I told ya Mugman took to reading like a fish to water, once Elder Kettle taught us to do some of it. Well, sir, since then Mugman tried to read anything and everything he could get his hands on. Sometimes I’d catch him bent over a newspaper, muttering to himself. I thought he was crazy, but he was just reading. He was one of them newsies, you know, the kids who stand on the streets and yell at ya to buy a paper. When business was slow and he couldn’t sell, he just practiced his reading. Real smart kid. 

Well, between my soul-crushing job and Mugman’s newsie gig, I was getting downright depressed. The stress of trying to put food on the table, trying to pay rent, trying to support my brother, trying to keep from starving, all of it was weighing down on me. I knew no matter how hard we worked we just plain weren’t getting enough to eat. I was getting sick of the whole business. I’m ashamed to say it, but I began to drown my sorrows in drink. The stuff was cheap, and when I had a few spare coins I figured I’d just “treat” myself, ya know? Just one drink. And then two. And then three. One more won’t hurt. 

It was around that time when I was starting to lose myself in drink that I started looking over Mugman’s newspapers that he brought home sometimes when he couldn’t sell them. I didn’t bother reading much, but I liked the pictures. By and by I happened to notice the same guy popping up now and then in the local section of the papers. He was kind of a pudgy fella, lookin’ like most toons around, except he had these slicked-up horns atop his head, and a real toothy grin. He was always grinning up from the page like he had just told a funny joke at a party. I’d come to know that damn grin pretty well, soon enough. 

According to the article, this Bendy sure lived up to his demonic nature. Before prohibition, he worked as an intimidation thug, bullying people into voting for whatever politician was paying him. Then he was involved in some big gangs that extorted money from prosperous factories and shops. The newspapers gloried in the intricate details of corruption, bribery, money laundering, prostitution, and just plain badness that Bendy was involved in. As far as I was concerned, the demon was doing God's work; I had no use for a law system that didn't protect young boys from the horrors of child labor or capitalists who practically starved their replaceable workers. No sir, if the whole damn society came toppling down I would dance on its corpse. 

I came to view Bendy as a kind of rebel: someone who was actively working against the system. Oh, I knew he wasn't a good guy by any means, but I couldn't help being fascinated by him. It was just hard to believe that the guy with the goofy grin and horns slicked up like a teenager at prom was actually the head of a real mafia gang. Bendy seemed like the kinda guy I wanted to be: smart, confident, cocky. Powerful enough to take down anyone. Rich enough to bribe the rest. And smart enough to keep it all going!

Once, I actually saw him. In a little black automobile, just a few streets from my own. I'd stared at those horns often enough to recognize them anywhere. The car drove away before I could get any closer. But after that, I kept on the lookout for him. I knew Bendy's gang was active in my neighborhood, but I didn't know where exactly. Walking to and from work, I looked for that car. I started following anyone who looked suspicious. And whenever I had off from work, I looked for clues to his hideout. Got pretty close, too. I started watching guys down at the port; I’m sure they were smuggling stuff in. I admired Bendy the way a child admires some storybook hero: as someone fantastical. I was sure I'd never actually meet him. 

Of course, that didn't stop me from imagining meeting him. It wasn't an obsession, exactly. More like a hobby. I needed something to distract myself from my soul-crushing work and worrying about Mug and stress about paying bills. I could barely get enough food to feed my body. I needed something to feed my soul. So I made a game out of searching for Bendy's hideout, like a real detective would; trailing guys and following clues and hiding where I could spy without getting caught. It gave me some feeling of my old adventures when I was a kid. But it was nothing more than a game. 

Until it wasn't. 

My amateur detective work took me pretty far out of my neighborhood and uptown to the wealthier part of the city. It was late afternoon and I was walking along, pretending I belonged there, when I stumbled across Bendy’s headquarters completely by accident. 

I was just scouting out the place for investigating, thinking there was no way I’d get anywhere in this part of town. But then suddenly, there was that familiar black car across the street and there was him, curved horns just barely visible above the car. Holy mother on a popsicle stick. I wasn’t even looking and there he was! It took me a minute to get my senses back, I was so startled. Better act fast, so I started following without even thinking. 

Bendy walked to the side door of a tall luxury office building, flanked by his thugs. They were tough looking customers, with weird misshapen limbs and mismatched eyes. They were both bigger than Bendy, but were clearly quite loyal to him, judging by the way they kept their guard up even though there was hardly anyone else on the street. 

The thugs waited outside while Bendy disappeared into the side door. They must’ve been keeping watch to make sure he wasn’t disturbed. I moved quick and stealthy, ducking behind the car and then waiting for an opening to get closer. I was just trying to get a closer look in that side door, ‘cause I was sure it was his office or something. Just had to get closer without getting caught by the guards. Gosh, I was just about trembling with excitement. I was sure I was on the verge of some big breakthrough. I didn’t know what I’d do with that information, but the thought of having it made me feel so powerful. 

Bendy called out something from inside the building, and one of the thugs, the one with several arms, walked towards the car. I took my opportunity and moved closer, jumping behind a mailbox. I was just about ready to move again, my breath coming rapidly with adrenaline, when a loud voice cut across the street. 

“HEY!” 

It was so close it made me jump two feet in the air, and when I regained my bearings the guard at the door was walking towards me. Shoot, I underestimated how close I was to the door! Stupid! But before I could run he had caught up to me. 

“What the hell are you doing here, huh?!” the guy shoved me hard to the ground, and I scraped my hands on the rough cement. Now, I just wasn’t gonna take that lying down. When a guy shoves me, I shove back. That’s just the way the world rolls. So when he came closer to grab me, I punched him real hard in the gut. 

“Nngh!” he grunted and recoiled from the hit. I took that as a chance to retreat, but as I turned he grabbed me from behind and lifted me up. I could tell this guy was used to bullying weaklings, the way he grabbed me by the waist like a lady waltzing with him. He wasn’t prepared for a tough guy like me. Growing up on the streets of Toontown, I knew how to defend myself. So I yelled at him to let go and when he didn’t, I stomped hard on his misshapen lump of a foot. We were still scuffling when the thug with several limbs returned from the car.

“Get ‘em, Striker!” the guy fighting me yelled, and they both jumped into action. It was two against one now, and I was ready to fight tooth and nail. Turning toward my first attacker, I shoved my knee into what I assumed was his crotch and that put him out of commission for a bit. Striker pulled a baton outta nowhere and swung fast, hitting my shoulder. Ignoring the pain, I seized the end of his baton and used the momentum of his swing to slam him hard into the wall of the building. There was a loud thud when he made impact and slumped against the ground. 

Of course, that was the exact moment when Bendy walked out the door. 

“What the hell is going on out here, Piper?!” he hissed angrily at my first attacker.  
I was so startled by his sudden appearance that I let my guard down. Piper took the opportunity to jump over and pin my arms behind me, forcing me to my knees. 

“I caught this kid spying,” Piper explained, panting from the exertion. “And he put up a fight. Looks like he hurt Striker real bad, too.” 

“That so?” Bendy’s gaze fell on me, and I stopped struggling against Piper’s hold. Holy heck. He was actually right here, in front of me, and I had no idea what to do. 

There was no sign of the goofy grin that I was used to seeing in the papers. Bendy’s face was twisted into a nasty sneer as he leaned in close to my face. “And what do you think you’re doing here, hm?”

I’m not exaggerating when I say that my reply changed my life forever. 

“I’m here because I want to work for you.”


	2. Shortcuts

**Notes for the Chapter:**

> For this chapter I really wanted to play around with the idea of an unreliable narrator. Bendy reluctantly tells us his side of the story, but how much do you really trust him? I had a bit of trouble with the transitions so I hope it flows okay. Constructive criticism is appreciated!
> 
> Chapter warnings: None

Bendy’s POV

I’m glad Cuphead started the first chapter and not me. He’s so honest; practically wears his heart on his sleeve. I’m not honest, even with myself. I keep too many secrets. 

I’m not sure I agree with Cup’s metaphor though. “Being a hero is like standing on the edge of a cliff”. Yeah, some people jump all the time, and others never do. But the smart people find a safer way to reach the bottom. They go around the cliff. Problem with that is, you miss the beautiful view. 

Cuphead showed me how to appreciate the view, even as we fell through the air. 

My name’s Bendy, and this is how I learned to love the view. 

I was born into an old-fashioned, wealthy family, who wasted no time shipping me off to boarding school in Europe. There, I was given the finest education and got perfect grades in all of my classes. Unfortunately that did not win over my classmates, who took great pleasure in tormenting me, and…

Hmm, nah, that’s not nearly sympathetic enough. Let me try again. 

I was born on a dark and stormy Halloween night. My father rode out to fetch the town doctor, five miles away. My mother, dying from childbirth, raised my tiny body to the heavens and prayed for God to save her baby. 

I told that one to the cops once, and even they didn’t buy it. Let me see…

My parents raised me in a dark, isolated swamp. I stayed away from society, ashamed of the monster that I was. That is until I met a talkative but loyal donkey played by Eddie Murphy--

Wait, that’s Shrek. 

Okay, okay, how about this one? 

I was born out in the midwest, in a small mining town far from any civilization. My parents were hardworking, decent folk. They were poor, but they did alright for themselves. The only thing that marred their plain life was that they had no children. Try as they might, the couple despaired of ever having a child. Becoming increasingly desperate, they ended up turning to the one source they knew would not fail them: they made a deal with a demon, unaware of the hellish power they would unleash upon the world by doing so. 

Haha, okay, even I don’t believe that one. After all, everyone knows demons don’t exist. 

There I was, a young kid standing on the edge of Toontown, the biggest city this side of the planet. If you wanted to be something, Toontown was the place to do it in. I had a little money in my pocket and enough confidence to move buildings. I immediately hit up all the bars, clubs, saloons, and other such type places to see about getting on their stage. I had talent. I could crack a few jokes, sing a little. Even tap out a little dance or two. But most owners immediately pegged me for what I was: some small town hick looking to make it big in the city. At least one guy was sympathetic: Boris, the clarinet player at this ancient bar called McSorely's. He was a tall, lanky fellow with long nimble fingers and a mechanic's brain. Playing at that little dump was his only source of income; mostly, he just liked doodling weird mechanical inventions. 

Boris and I found we got along quite well. He was raised in the city and knew it well enough to show me around. He even let me sleep on his couch, which eventually extended into my living with him. He was a laid back, kindly old soul. Seems like he was just delighted to have someone around to talk to. For my part, I regaled him with fantastical stories about growing up out west. Some of them I made up on the spot, but he didn't seem to mind. Some fellows are just happy to let you run on your own script.

Naturally, Boris helped me land a job at McSorely's. I sang and he played the clarinet, and I must say we sounded pretty dang good. Even better, I met other guys on the show biz track, and they were more than happy to give a newbie some tips. Learn how to read your audience, an opera singer told me. Get a feel for the mood. You have to watch them just as much as they’re watching you. Pretty solid life advice, and it helped me establish connections with the right people for later on. Seemed like my acting career was really picking up. Sure, the pay wasn't great, and Boris preferred to sketch machines and gears than practice, but I was sure we were on the right track. Eventually, I thought, I'd move on to bigger and better things. 

Then disaster struck.

One morning, I was making breakfast in the small kitchen we shared when Boris walked in. He was not his usual cheerful self, but uncharacteristically silent. Without a word he passed a short letter across the table for me to read. It was from his sister, who lived with her husband and children in Inkwell City, halfway across the country. It explained, briefly, that her husband was killed in a car accident, leaving his wife and children without financial support. Boris would have to move there to help them. 

By the time I read the end of the letter, my blood turned to ice and I was trembling all over. Boris was going to move. Boris was going to leave me. My best friend, my partner, the first guy who was kind to me in this city. Without his musical talent, my acting career was finished. Boris mourned his brother-in-law, but mostly he hated to leave the city where he had grown up. 

"What am I supposed to do?" He asked gloomily. "I can't just leave her and the kids alone. They don't have the money to get by." 

"Money…?" I perked up, an idea forming. "If we sent them enough money, would they be able to get by without you?"

"Well, yes, I suppose so," said Boris doubtfully. "But that would have to be an awful lot of money, Bendy. Where would we get that kind of dough?" 

"We'll find a way, pal," I said firmly. "I promise." 

With a goal firmly in front of me, I got right to work. I had to find a way to get that money, and not just for the sake of my acting career. Boris was my best friend. He gave me so much kindness. I was determined to give back to him, somehow. Problem was, I needed a lot of money, real fast. 

Maybe I could’ve raised the money myself. Would’ve taken a long time, but maybe I could have done it legally, ethically. Who knows? I’ve always preferred taking shortcuts.  
This was where my acting connections came in. Since I needed a rather illegal solution to my problem, I was careful as to who I asked and who I would trust. This was before Prohibition, so there were no organized gangs to turn to. I would have to depend on individual friends who could connect me to the right people and wouldn’t turn me over to the police. Although I really trusted some of the guys I asked, my hope was stretched thin. How was anyone supposed to get me the kinda money I needed in so little time? Boris morosely set aside his drawings and searched for another job. For a while both of us were seriously down in the dumps. That’s why it seemed like such a miracle when a burlesque dancer I knew introduced me to Mister Joey Drew. 

He was the sorta guy you could easily pick out of a crowd: tall and remarkably slender, but not lanky. He held himself up so straight you thought he had a steel rod in his back. And he had this incredibly long, curly mustache; his only vanity, he called it. And he was infuriatingly clever, a smooth talker, a silver-tongued slimeball. Whatever you want to call him, Joey Drew was just oozing with charisma. He never put in more effort than he had to; he was the master of shortcuts. We met at a crowded bar just off of Main Street. He bought me a drink and did most of the talking, which I was fine with. Like I said, he was a smooth talker. Just listening to him was a pleasure; he was so eloquent. And by the end of our little meeting I had a job in a loan shark gig. 

The beginning of my criminal career wasn’t particularly remarkable. Mostly I did menial jobs for the other guys, ran errands and acted as extra muscle. But as I did more of it and rose higher on the ladder, I started to enjoy it. You see, acting is a lot like lying. You have to be able to transform yourself into something you’re not, and I was already real good at that. I wasn’t any kind of criminal, not by a long shot. But as long as I pretended to be a criminal, to talk tough and push guys around, it got a lot easier to actually be one. The audience might see what you want them to see, but no one has to know your mind is still running through the script. And eventually, the script becomes natural. 

I won’t get into the details. There are some things I shouldn't talk about and some names I shouldn’t name, out of respect for the dead and living. Suffice it to say that I rose up through the ranks, and when Prohibition hit, I just rode that wave to success, the best shortcut of them all. Pretty soon I was sending monthly checks to Boris’s family. Boris himself was grateful that he could stay in the city, but I wasn’t interested in our performances anymore. I was working full time in organized crime, picking up on the trend of smuggling alcohol that had seized the country at the time. I even arranged for Boris to get a job in construction, so he could have the time and resources to work on his wacky inventions. Even as my network of allies and connections grew, Boris remained, and still is, my best friend. Sure, we had our differences; mostly that he didn’t approve of the things I was doing. But I was lucky to have him. 

Then there was Mister Joey Drew. He took a shine to me for some reason; maybe I reminded him of himself. He guided me around the various Mafia intrigues, taught me how the police work, things like that. You could call him a mentor, a teacher, maybe even a father figure. He was a genius when it came to people. He always knew just the right thing to say, how best to tell someone bad news, and how to appease even the worst attitudes. We once went to a poker game where he taught me about people’s ‘tells’: the little things they do when they’re lying. It could be anything from quicker breathing to blinking really fast. Yes, I learned a lot from him, and I’m grateful for everything he did for me, even when he...ah, I’ll get to that later. I’ve already said too much. 

I don’t like talking about this stuff. It brings back bad memories. Not that I’m ashamed of it or anything, but. I don’t know. The only one who’s ever really heard it in full was Cuphead, because I knew he wouldn’t judge me. He’s not innocent either. Now, if you don’t mind, I better pick up that story of how Cup and I met. That’s a lot more interesting than my past, anyway. Really, how much backstory does one guy need? 

\--------------------------------------------------------------------

“I’m here because I want to work for you.” 

I stared at him, this cup guy who was pinned down by one of my men and still had the guts to look me in the eye. If he didn’t look so serious, so determined, I would’ve thought he was absolutely insane. 

“You...want to work...for me?” I repeated in disbelief. The whole scene was so strange I just started laughing. I couldn’t help it. Piper, who was holding the cup, started laughing too, but I think it was for a different reason. 

“Psht. This ain’t an employment agency, bud,” Piper scoffed, an ugly smirk on his face. He roughly shoved the cup to the ground. “You don’t come to us, we come to you. Now gimme one reason not to--” 

“Easy, Piper. ” I warned playfully, watching the cup scramble to his feet. By now my gun and Piper’s gun were both aimed at him, and as he stood up, he quietly raised his hands in surrender. “The guy’s got guts, let’s at least hear him out. What’s your name?” I added, turning towards him. 

The cup hesitated, perhaps surprised at being asked such a casual question after such an intense encounter. “Cuphead,” he said carefully. “And I--” 

He was interrupted by a low moaning sound, and all three of us turned towards it. It had come from Striker, who was still slumped against the wall and just now coming to. Damn, I forgot about him. I quickly walked over to him and examined the wound on the back of his head, where he had made impact with the wall. It was a large gash, but messy, as though it had been done by accident. Clearly this Cuphead had a lot of power, but he was untrained and uncontrolled. 

“Piper, get him inside and give him medical care,” I ordered, indicating the injured Striker. “I’ll take care of this spy.”

Piper hesitated, not wanting to leave me alone with the intruder, but he obeyed and carried Striker through the door. Good man, Piper. 

“Hey-- I’m not a spy!” Cuphead protested, offended at the mere thought of the idea. 

“No, you’re not-- a real spy wouldn’t let himself get caught,” I returned snappily. You have strength, but you don’t know how to use it. You need discipline. A real gangster wouldn’t throw himself into this situation.” 

Cuphead looked like he was about to argue, but thought better of it. “Look, I’m not a real gangster,” he admitted. “Not yet. But the way I’m going now, I’ll never amount to anything. I know what you do, and I want in on it. If you think I need discipline, then I know you’re the one who can do it.” 

His words were humble, but his eyes were blazing with...I don’t know, dignity? Confidence? Determination? Whatever you call it, it was not something that could be ignored so easily. That kind of courage is hard to come by these days. See, most criminals, myself included, are self-serving spineless cowards. But this guy was just aching to be some sort of hero, to get some action. I sure as hell could use someone like that around. 

“Hmm…well, I will need a new bodyguard, since you so kindly put Striker out of commission,” I said sarcastically. “What the hell. Maybe you got what it takes.”

The liquid in his head sloshed around audibly as he looked up, hopeful. “Really?”

“Of course not, I don’t just let in anyone with a good left hook and puppy dog eyes,” I chuckled. “I’ll have to talk it over with the other guys. In the meantime, you can come along on some jobs, alright? Just so I can keep an eye on you. Sneaking around gangsters is a great way to get yourself, killed, you know.” 

“Well, it got your attention, didn’t it?” Cuphead smirked. 

That surprised me. He wasn’t just some adrenaline junkie: he had planned this out. Hm. Maybe he was smarter than I first gave him credit for. All the better: it made my decision much easier. I still kept my gun in hand, however. 

“You realize, of course, that if you’re lying to me, or you make any wrong move, you’re finished,” I informed him cheerfully, gesturing towards the door with my gun. 

“I wouldn’t lie to you, Bendy.” He winked at me and stepped, hands still raised, through the side door. I followed him inside. 

This was my office. Not much to look at, but it does it’s job and, for all intents and purposes, it’s home. Used to be a therapist’s office, and still had most of the furniture. A bunch of my guys were lolling around on some battered old sofas. They played cards, smoked, talked. Striker was also laid out on a sofa, getting his head bandaged by our resident medic. Later that evening the group would head out to be muscle on some jobs I needed done. But right now they were taking a break. My guys are an ugly lot: misshapen and disabled, with sour attitudes to match. The outcasts of society. Decent people might not have them around, but I’m not decent, and they get the job done. 

I pointed Cuphead past those guys and towards my office, but we stopped by my secretary’s desk. There worked a beautiful woman, with long black hair and a permanent scowl. Alice Angel was a good friend, and an even better lover, when we had dated briefly. Now she looked down her nose at us. I saw her clever eyes flit from my suit to Cuphead’s patched-up old pants, and her usual frown curled in disgust. Clearly she didn’t approve, but she didn’t approve of a lot of things I did. 

“Alice, this is Cuphead,” I introduced them gallantly. “Cuphead, meet Alice Angel, my lovely secretary, and the real backbone behind this operation.” 

“Flattery will get you nowhere, Bendy,” she tossed her hair irritably and marked something on a notebook in her desk. “What’s he here for?” she eyed Cuphead suspiciously. 

“He’s my guest, of course,” I replied smoothly. “Just showing him the ropes, you know?” I winked at her, but she didn’t get the humor and merely waved us away. 

“Nice to meet you, ma’am,” Cuphead politely called back to her, and I couldn’t help but smile. I wondered how long it’d been since Alice was called “ma’am.” 

As we stepped into my private office, Piper followed us in; as my bodyguard he’s supposed to follow me around at all times, especially with this stranger here. You couldn’t ask for a more loyal fellow than Piper, but the man had no sense of humor. I had made it a personal mission to try and make him laugh or smile, but so far no luck. 

Piper closed the door behind him, so the three of us were alone. Cuphead looked at me expectantly, almost nervously, as though afraid we might think it better to off him behind closed doors. 

“Gentlemen, I brought you both in here because we have a problem,” I began. 

“It’s the missing cops, isn’t it,” Piper muttered under his breath. 

“Don’t interrupt. But yes, it’s the cops. Several patrolmen have gone missing the past few weeks,” I explained to Cuphead. “And we wouldn’t care so much except all of them were last seen at the docks, near our activity, which means we’re getting the blame for it. Normally the cops are kind enough to look the other way for us, but they can’t ignore missing men. You know--” 

I was interrupted by the loud ringing of the telephone near my desk, and Alice’s voice penetrated the office door. “Commissioner Pete on the phone for you, Bendy.” 

“Speak of the devil,” I grumbled under my breath. “Excuse me, gentlemen, I have to take this.” I picked up the earpiece and braced myself for the onslaught. 

The dear commissioner is not one to disappoint. “YOU BLASTED LIL RAT!” a familiar voice bellowed through the phone, so loud I had to hold the earpiece away from my head. “THAT’S THE SIXTH COP GONE MISSING THIS MONTH! WHERE ARE THEY, HUH?! YOU BETTER WISE UP OR YOU AND YOUR WHOLE RAT’S NEST ARE--”

And on and on he went. Piper rolled his eyes, accustomed to chief Pete’s ranting, but Cuphead listened with wide, fascinated eyes. I could practically see the adrenaline building up in his body. 

After a minute of yelling Pete began to run out of breath, and during his pause I took the opportunity to hang up the phone. I sighed and looked at the other two. “You see what I gotta deal with?” 

“He’s the police chief, why doesn’t he do something about it?” Cuphead asked indignantly. “I’m sure he’s got plenty of detectives looking for them.” 

“Because they’re just waiting for a chance to nab us,” I frowned. “Somehow, they’ll find--or fabricate--evidence that will point to us as the culprit, and then where will we be? The cops may be corrupt as hell, but we gotta play by their rules--for now. That’s why we’re going to do a little detective work ourselves and stop police from going missing before they find a way to pin it on us. You boys in?” 

The difference between the two was remarkable: Piper merely nodded grimly, but Cuphead was practically shaking with excitement. “You got it, boss,” he grinned and gave me a thumbs up. Well, this was sure to be a very interesting little investigation. 

Without further ado we filed out to the car. Cuphead bounced ahead, of course, so while he was distracted I grabbed Piper’s shoulder and held him back. 

“Keep a very close eye on our new friend there,” I whispered in my bodyguard’s ear. 

“You suspect something’s up?” Piper whispered back. 

"Not yet." I gave him my signature grin. 

"But ceramic is very easy to break."


	3. The Demon Rises

**Notes for the Chapter:**

> Hope ya'll had a fun and safe Halloween! Have a spooky chapter <3
> 
> Now that we're done with the main backstories, this chapter is more plot-focused and a bit action-heavy. I hope you enjoy reading it as much as I enjoyed writing it!
> 
> Chapter warnings: Ritual murder, Satanic worship, swearing

Cuphead’s POV

Later on I would learn that my presence in Bendy’s office and a well-placed note on Alice Angel’s desk set off a chain of events that resulted in my getting hired. 

Around the time that Bendy, Piper, and I left the office, two of Bendy’s men left as well, with clear instructions. They headed first to Toontown’s City Hall, where Bendy’s contacts there gave them easy access to my birth certificate. Going off of the information there, they went to Elder Kettle’s orphanage and questioned him about my work and character. They explained that they were looking to hire me for a job and needed references. The guys also found my criminal record; I’ve got minor offenses but nothing too crazy. They even tracked down my brother Mugman at our apartment and questioned him too. 

This is all to say that in less than 24 hours Bendy’s gang knew more about my life than I know about myself. There was no going back now. They ended up hiring me, and that meant I was committed. 

Of course I wasn’t aware of all that at the time. I was in a car heading towards my destiny. Bendy sat up front with the driver, Piper and I were in the back. It was gonna be a long ride to the harbor where our little investigation was supposed to happen, so I had plenty of time to stare out the window and think about what I’d gotten myself into. My mind was still trying to process everything that just happened: the fight with the guards, meeting the guy I’d been fascinated with for months, and now I was actually going with him on a job! The kid in me, the adventure-loving rascal, was jumping with joy. The whole thing still felt like a game, like my innocent detective work. Except this time I wasn’t hiding, safely at a distance. I was in the middle of it, and I couldn’t have been happier. A real genuine mafia gang! Won’t Mugman be impressed! 

Mugman. How was I going to tell him I’ve joined organized criminals? Would he be angry? Scared? We’ve gotten in trouble before, but that was mostly when we were kids. This is big boy stuff. I could go to jail for years, or get killed, and then who’d look after Mugman? Oh no. I’d been so wrapped up in my own excitement I didn’t think about how my brother would be affected. I could already hear him scolding me, calling me reckless and selfish and stupid, and I’d have to take it because I know it’s all true. Some brother I turned out to be! Where would Mugman go if something happened to me? I guess he could go back to Elder Kettle, but--

Thankfully, my anxious thoughts were interrupted. Someone in the car was whistling a soft, familiar tune, just loud enough to be heard above the traffic. I looked around. Piper, next to me, was motionless, staring out the window with hard, unblinking eyes. The driver, a bearded old codger, was smoking heavily from a pipe, so it must be Bendy, sitting in front of me. I listened to his whistle a little bit longer before I remembered what song it was. 

_Pack up your troubles in your old kit-bag  
And smile, smile, smile.  
While you’ve a lucifer to light your fag_ (cigarette)  
_Smile, boys, that’s the style.  
What’s the use of worrying?  
It never was worthwhile.  
So pack up your troubles in your old kit-bag  
And smile, smile, smile. _

Gosh, but I haven’t heard that song in years. It’s an old-timey tune that was pretty popular back in the 1914 war. Elder Kettle used to sing it to us when we were little, like a lullaby. Hearing it again made me smile for the memories I associated with it. Happier times. 

“Hey, I know that song,” I said a little too loudly. “‘Pack Up Your Troubles’, right?” 

Piper didn’t move, the driver kept driving and Bendy stopped whistling to answer. 

“Yeah, it’s an old war song,” he said cheerfully. “I’m surprised you know it. Most people don’t, these days.” 

I explained that I’d heard it as a child and had nice memories associated with it. He replied that he’d heard it on the radio when he first arrived in Toontown, some years ago. It was pretty hard times then, he said, being new in the city and not quite knowing where to go next. Hearing the song with it’s catchy ‘smile, smile, smile!’ lyrics were comforting during those tough times. 

We made some more idle conversation: I told him about growing up in the orphanage and the kind of trouble we used to get into. Bendy told me about his early years in the city and some funny anecdotes about being an actor. We found that we both had a pretty dark sense of humor: I told a grim joke about city rats that usually makes Mugman squirm, but Bendy laughed at it. I mean like really laughed. He thought I was genuinely funny. Talking to him was nice because he’s one of these guys that’s really, incredibly good at listening. I mean when you talk to him, he gives you his entire attention and makes you feel like the most important person in the world. It’s one of those things that makes a good leader, and he knew it too.  
Too soon the car screeched to a halt and we got out, leaving the driver to smoke and scratch at lottery cards. Immediately the smell of salt and fish assaulted my nose. That’s how you know you’re at the harbor. The salt comes from the sea, where huge-sailed ships are docked, bringing in or taking on cargo. The fish comes from the massive fish market, which is always crowded with people buying, selling, and generally having a good time. Sailors walked down the busy streets flashing their exotic tattoos and telling long yarns to anyone who’ll listen. The harbor’s always lively and bustling with traffic and people and fish, especially now with the late afternoon sun beating down. Even at night it gets busy. That’s when guys like Bendy meet with certain ships to smuggle in illegal alcohol, usually from Canada or Britain. It’s supposed to be a top secret operation, but most everyone knows that’s how the speakeasies get their liquor. It also explains why cops would go missing around here: obviously someone didn’t want patrolmen interfering with their bootlegging. 

“Why, though?” I mused aloud as I followed Bendy and Piper down the busy streets, where we blended into the crowd easily. “Missing cops would just bring the authorities down on you. No one would do something stupid like this unless they want to attract attention.” 

“That’s what I’m thinking,” said Bendy grimly. “I don’t believe it’s a rival gang. Missing cops puts all of our operations in jeopardy. So it must be someone on the outside, someone trying to get us in trouble.” 

“Where to first, boss?” Piper grunted. 

“A guy I know has a bookshop down here,” Bendy answered. “He sometimes hides alcohol for us after we bring it in from the boats. We’ll check on him first, see if he knows anything about it.”

We walked a few blocks before reaching a squat storefront with the words “SAMMY’S BOOKS” handwritten in neat cursive above. Bendy strode in confidently. A little bell clinked on the door as we walked in. The store inside was old and dusty and small, with rows and rows of cramped bookshelves stacked so close together you could hardly walk through them. A few people, probably escaped from the busy harbor streets, were idly milling about and browsing books. An ancient grand piano was stuffed into a corner behind the bookshelves. It was covered in fingerprints and scribbled papers. Somebody around here wrote music. 

“Oh! My dear Bendy, it is a pleasure to see you,” an unfamiliar voice sang out, and the titular Sammy stepped out from behind the counter. “To what do I owe this unexpected visit?” 

I stared; I couldn’t help it. This Sammy guy was another of the many strange people Bendy worked with. His skin was black, entirely inky black, with no recognizable facial features except a pair of glowing white eyes. I don’t know how he spoke without a mouth, but his voice was smooth and refined, like the classical music he probably played on the piano. He was dressed plainly, in a white buttoned shirt and work pants, but they looked good on him, somehow. He was essentially charismatic, despite not having proper facial expressions. His hands, which gestured a lot when he spoke, did most of the expressing for him. 

“Lawrence, I promise you one day I’ll come in here to actually buy a book,” Bendy grinned at his own joke, “But today is not that day. I’m sure you’ve heard about police going missing around the harbor area?” 

Sammy’s eyes seemed to glow brighter. “Yes, indeed. Rather unfortunate incidents. It doesn’t look good for the authorities to lose their men so easily.” 

“Doesn’t look good for me either,” Bendy replied. “You wouldn’t happen to know anything about it, would you? I mean, you work at the harbor all day. You must have seen something.” 

Sammy Lawrence hesitated, rubbing his chin thoughtfully.”Well, now that I think about it, I might be able to provide a clue or two. Two nights ago I was trying to take some photographs of the harbor with one of those new Kodak cameras, to send to my relatives.” 

“Two nights ago?” Piper interrupted. “That was when the last cop disappeared.” 

“Precisely,” Sammy gestured eloquently. “It is possible that my photographs may have caught an image of the incident, though it is a slim possibility.” 

“It’s better than nothing,” Bendy declared. “Let’s see those photographs.” 

Sammy smiled, or at least I think he smiled. His eyes crinkled like he was smiling. 

“It will be my pleasure, dear Bendy. Please, follow me; the film is downstairs.”

The three of us followed Sammy through a back door behind the counter, leaving the bookshop behind. As we descended deeper, the stairway grew darker and darker. I wondered why Sammy hadn’t bothered to string up electric lights here; it was getting so dark I could hardly see my own feet in front of me. Abruptly the stairs ended and we were in the basement, where a fantastically strange sight lay in front of us. Now, I’ve seen a lot of weird stuff while working with Bendy, but this was definitely one of the strangest scenes I have ever borne witness to. 

The basement was much larger than the bookshop above. It was a wide room with no windows and no doors besides the one we came through. There was no light except for small flickering candles scattered around the room. It took a minute for my eyes to adjust to the darkness, and that’s when I saw the giant black pentagram painted on the floor. At each of it’s corners a person stood, or at least I think they were people. Their faces and bodies were totally obscured with long robes and hoods. All of them were swaying slowly and chanting in low voices: 

_“The demon will save us...the demon will save us...the demon will save us….”_

Oh, and here’s the real clincher: They were all wearing masks with Bendy’s face on them. All of them wore that iconic grin that I knew so well. All of them looked at me with Bendy’s eyes. At first I thought, or hoped, that I was wrong, just seeing things, but those horns were unmistakable, and I only know one demon. 

“You have...a cult?” I breathed slowly. “You have a FUCKING CULT?!” 

As I turned on Bendy I realized that he was literally trembling with fear. 

“I-I didn’t-- I meant--” He was shaking so hard he couldn’t form proper sentences. 

Before I could respond, something large and hard made a blunt impact with the side of my head. I gave a small cry and went down fast. It wasn’t strong enough to knock me out, but it made a crack for sure. My vision blurred as unknown hands grabbed my arms, pulling roughly, and I was too dizzy to fight them off. Through the blur of pain I could see the hooded guys had got Piper too. They took his gun and dragged him off to one side of the room. Their Bendy masks were even creepier up close: blank, soulless eyes that seemed to follow me. We were too out of it to fight back as they handcuffed us to some kind of pillar, a support structure that stretched from the ceiling to the floor. My head hurt like hell, but I had got enough of my sense back to see the next horrifying scene: 

Six bodies were laid on the floor, stretched out across the pentagram. None of them were moving. I had to squint at them, from where I was handcuffed, and my heart dropped into my stomach. They were all wearing police uniforms. 

“Missing cops,” Piper muttered beside me, coming to the same conclusion that I did. My mind was racing feverishly. What was happening? What did these hooded freaks want from us? And why did they take those policemen? Were they still alive? Or were they--

“What the hell is going on here, Lawrence?!” Bendy’s voice cut across the basement, high-pitched with terror. “Lemme go, damn you!” He too had been grabbed by the hooded men, his gun taken away. I watched with horror as Bendy, the guy I was apparently supposed to protect, was forcefully strapped down onto a filthy leather chair. 

Sammy Lawrence stepped in front of Bendy, where the light from the candles shined the most. He was now wearing a Bendy mask too, his white eyes glowing brightly beneath it. He chuckled, a low evil sound. 

“We wouldn’t want our sheep roaming away now, would we?” he said, stepping closer to Bendy’s face. “No, we wouldn’t. I must admit I’m honored you came down here to visit me...it almost makes what I’m about to do seem cruel.” 

He turned away, now addressing the other hooded guys. “But the believers must honor their savior, yes?” 

_“The ink demon will save us,”_ The hooded ones echoed. _“The ink demon will save us!”_

“You’re insane--” Bendy began, but Sammy talked over him. 

“Arise, ink demon!” He raised his hands to the ceiling, his voice trembling with true faith. “Arise and claim our offering! We have gathered for you here the flesh of these men,” he gestured towards the policemen’s motionless forms. “These miserable wretches who in life hindered the work of our lord. But in death, they will be but mere sheep for the hunger of the demon.” 

_“Sheep, sheep, it’s time for sleep,”_ the hooded ones chanted, as though reciting a psalm. _“Rest your head, it’s time for bed. In the morning, you may wake. Or in the morning, you’ll be dead.”_

“Our lord is calling to us, my little sheep,” Sammy continued, addressing no one in particular. “The time of sacrifice is at hand. The ritual must be completed.” 

It was at this point in his speech that my anger and fear reached a boiling point. If there’s one thing I can’t stand, it’s guys being pompous and pretentious for no good reason. I still had no clue what was going on, but listening to this guy monologue about sacrifices and demons made me want to punch him in his stupid non-existent face. I was still handcuffed, however, so I had to content myself with shouting, much louder than I actually intended: 

“Hey, shitshow! You can go shove your ritual up your ass!” 

As soon as I said it I wished I could take it back. Sammy stopped talking, and the basement went deadly quiet. Suddenly everyone, Bendy, Piper, Sammy, and the hooded ones were all staring at me. I swear I even saw one of the policemen twitch. After a few seconds of uncomfortable silence, Sammy spoke between his (non-existent) teeth. 

“Very well. We’ll start with the small one.” 

Quickly and efficiently, one of the hooded guys withdrew from his robe a long, sharp knife and handed it reverently to Sammy. As the blade passed through the light of the candles, it looked as white and shiny as Sammy’s eyes. He grasped the handle confidently, and I could tell that he knew how to use a knife, had even perhaps used this exact one before. And then he was walking towards me. 

“No! No, stay away!!” I struggled helplessly against the handcuffs. I tried to kick Sammy as he came close, but couldn’t get a proper angle. Suddenly he seized the collar of my shirt. I saw his white-hot eyes beneath the Bendy mask, merciless and blank. He raised the knife, aiming it directly above my heart. 

Oh my god, I thought. I’m going to die. I’m really going to die here. My brother’s face flashed before my eyes. I won’t even get to say goodbye to him… 

**“HEY!”**

The unfamiliar voice was so loud, so startling, that even Sammy jumped and whirled around in a panic. My mind, still braced to die, struggled to process the new horror in front of me. 

Bendy’s toony body had swelled to twice its size. His horns, sharper and pointier than ever, obscured his eyes, and his head was split open by a gaping maw filled with shark like teeth. Thick black ink poured off him in waves upon waves. Too much ink. It secreted from his body like sweat on a really hot day. The chair was gone, and so were his clothes. There was only ink, and the black, pulsing muscles of his body beneath it. He was simply not Bendy anymore. He was a true demon. 

**“You want the ink demon?!”** Bendy roared, his voice distorted by demonic echoes. **"WELL, YOU GOT ‘EM!”**

With that he raised his massive paw of a hand, and as he brought it down, chaos erupted. There were screams as the hooded ones ran for cover. Some of them were crushed beneath the demon’s claws, others rushed for the door. Splinters of wood and metal flew everywhere as Bendy’s body, too big for the basement, ripped through the floors and walls. He was so large that the motion of his hands alone created huge gusts of wind, extinguishing the candles and plunging us all into darkness. At some point, amid the screaming and destroying, the structure to which Piper and I were imprisoned came toppling down. We quickly slipped out of the handcuffs and rushed into the chaos. 

Somewhere in the darkness I heard Sammy’s voice again: “No! My lord! Stay back! I am your prophet! I am your--AHHHHH!” 

There was a noise that sounded quite satisfyingly like Sammy getting mauled, but I had no time to enjoy it. By the fractional light of the few candles remaining, I saw Piper take down a hooded one with his fists. The policemen’s bodies had been knocked about and tripped over. Sammy Lawrence was gone, as were most of the hooded ones. But the ink demon was still roaring, still blindly fighting enemies that were no longer there. Suddenly, despite the crack in my head and the horror of what was happening and the trauma of nearly dying, my mind felt as clear as day. Adrenaline rushed through my veins and pushed me to think. 

I realized that Bendy could not control himself; in this demonic form he was like an animal, feral and destructive. The ink that gushed from his body was slowly flooding the basement; already it was up to my calves. Bendy’s massive body alone was going to demolish the basement’s structure and bring the whole building down on us, if we did not drown in the ink first. The demon needed to be stopped. But the guns we had brought were lost in the ink,I had no weapon, and I was running out of time. The ink, flooding faster as Bendy’s rage grew, was up to my waist. 

So I did a really stupid thing, as usual: I rushed into a situation without thinking, with that reckless attitude that everyone always said was going to get me killed one day. This time it was going to save my life. I don’t know what possessed me to go with this insane plan I had, or even if it was a fully formed plan at all. 

I walked right up to the demon and shouted to get his attention. To my surprise, the dumb beast actually stopped waving wildly and jerked his mammoth head down towards me.  
And then I began to sing. 

“Pack up your troubles in your old kit-bag and smile, smile, smile! What’s the use of worrying! It never was worthwhile! So pack up your troubles in your old kit bag and smile, smile, smile!” 

I can’t carry a tune to save my life, but that didn’t stop me from belting out the lyrics I only half-remembered from my childhood. Out of the corner of my eye I saw Piper staring at me like I was absolutely insane, and he was probably right. The demon, on the other hand, was still staring down at me, quite still. 

“C’mon, Bendy, you know that song!” I pleaded desperately. “You were telling me about it today, remember? You heard it on the radio years ago! You remember how it goes, right, Bendy?” 

I don’t know what I expected to happen then, but I definitely did not expect the small tidal wave of ink that hit me full in the face. The stuff bowled me over, got into my nose and mouth, and for a moment I was terrified that my plan had failed, and that instead of being stabbed to death by a maniacal cultist, I was going to drown in ink. Maybe God just wanted me to die that night, I don’t know. But I didn’t. The ink receded quickly, draining into the basement’s plumbing. The place was a mess of extinguished candles, battered bodies and puddles of ink. And in the center of it was Bendy. 

Bendy, back to his normal size, himself again, was on his knees and breathing hard. After all that demonic rage, he looked small and vulnerable, like a mouse caught in a trap. Ink dripped down his face like black tears. Piper and I, being the only ones still standing, immediately rushed to his aid. Up close, I realized Bendy’s body was shaking uncontrollably, and he was hyperventilating. Instinctively I put my arms around him, because that’s what I did when Mugman had panic attacks. Piper, shockingly calm and efficient, pulled from the inside pocket of his jacket a long syringe with a sharp needle at the end. It was filled with a clear liquid, like water. Without hesitation he jabbed the needle into Bendy’s upper arm and injected the stuff inside. 

In answer to my puzzled stare, Piper said, “I gave him a dose of hydrogen peroxide. It helps get rid of the ink.” 

And indeed, even as I held him I felt Bendy’s muscles relax, and his breath slowed as the liquid worked through his veins. The adrenaline that had fueled my energy was gone, and I felt exhausted and aching. 

“This...has happened before,” I said weakly. Piper nodded stiffly, looked around the room, and stood up. I watched him approach one of the policemen’s bodies. He kneeled by it and lifted the left wrist, checking for a pulse. 

“They’re alive,” he announced. “Just heavily drugged. We need to alert the cops and get the hell out of here. Now.” 

I don’t really remember us getting out of that basement, pulling Bendy up the stairs, supporting him with our shoulders. Though he had stopped shaking, he seemed too weak to walk by himself. I don’t remember stumbling through the bookshop and heading outside. I didn’t even realize how suffocating it was in that basement until we had stepped into the cool night air, the dark clouds still hanging above as always. As soon as we were outside, Bendy heaved and vomited onto the sidewalk. Thick black clots of ink were expelled from his body, and then he seemed to feel better. He was able to at least walk a little, leaning on me for support. Piper, more clear-headed than I, found a telephone booth and called the police, instructing them where to find the missing cops but giving no other information. Then we walked back to the car, got Bendy into the backseat, woke up the driver, and headed off. 

“How did you know singing that song would calm him down?” Piper asked abruptly as the car’s engine roared to life. “Usually it takes more physical force to subdue the demon.” 

I shrugged. I truly, honestly had no idea. 

I sat next to Bendy in the backseat, just watching him. I had been fascinated by this guy, but tonight I had learned far more than I wanted to know, things scarier than I could have ever imagined. So I watched and waited for answers. 

Bendy opened the window and breathed in the night air as the car raced past the harbor, heading uptown. He knew I was watching him, knew that he couldn’t avoid my eyes for too long. After a minute I had enough of waiting, and said,

“So when were you gonna tell me about the whole ink demon thing?” 

He winced at my sharp tone. When he answered, his voice was surprisingly steady and firm. 

“I don’t know anything about those guys. Sammy Lawrence was just an...acquaintance.” He swallowed hard. “I don’t know how they found out about me--about the demon. They must have been planning this for a long time.” 

I didn’t say anything, and he didn’t look at me. He just stared at the back of the car seat and the words came pouring out of him like the ink from the demon’s body. 

“I’ve never made it a secret that I’m a demon. I’ve always been one. I’ve tried not to let it interfere with my life. But somehow it keeps on rearing its ugly head. The ink’s a part of it, part of the demonic power. It’s strongest when I’m really upset, or scared or angry. When I saw Lawrence going on about sacrifice, I couldn’t sit there and take it. I had to do something. He was going to kill you because of me. I let the ink demon take over.” 

He licked his lips and exhaled slowly. 

“The last time I went full ink demon like that was two years ago. My friend was murdered. He was more like a mentor, really. Joey Drew. He was the head of the gang before me, and he taught me everything I know about the business. He was a genius, and he was a good friend. And then he was murdered. By a rival gang. He had encroached on their territory, made a business deal that violated their rule in that neighborhood. So one day, as he was getting out of his car--” 

I watched the words get caught in Bendy’s throat. I was afraid the ink would start dripping again, just from his emotion, but he caught himself and continued. 

“When I heard he was dead, I couldn’t control myself. Joey Drew was like a father to me, you know? Someone...someone I loved. And he was ripped from me just like that, just because of a fucking business deal. I’m not proud of what I did then. But I stormed into their headquarters and ripped some of those bastards limb from limb. I didn’t get all of them. I didn’t even kill the ones that had done the deed itself. But I made them fear me. Oh yes, I made my reputation that day. After that, no one fucked with me or my people. Hell no. They value their spines too much. That’s the thing about this business. It’s never about the money, or about which gang owns that neighborhood or which son of a bitch has the most alcohol. No, this shit gets personal. Don’t ever let them tell you it’s about business. It’s not. It never is. It’s personal.” 

He paused to cough and spit ink out the window before continuing again. 

“Every night I get a dose of hydrogen peroxide to keep my ink levels low. It’s usually pretty effective, but when my life is in danger, when my men’s lives are in danger, all bets are off. I can’t control what the demon does. I only see red. I don’t know what it was about your singing that got through to me, but it did. That song reminded me of something better than myself. I don’t know. It was a really brave, really stupid thing to do. Well, now you know that I’m a monster. My bodyguards don’t protect me from anyone. They’re protecting everyone else from me. I’m dangerous to myself and everyone around me. You still want the job?” 

I did not hesitate. My choice had already been made. “Yes. Of course.” 

Bendy sighed deeply and leaned his head back against the seat. 

“Good, ‘cause if you tried to back out now I probably would have to kill you. And I don’t want to kill you. I like you too much.”


	4. Business As Usual

**Summary for the Chapter:**

> As time passes, Cup and Ben learn to trust each other. Still, their friendship is off to a rather rocky start...

**Notes for the Chapter:**

> Chapter warnings: Racism/discrimination

Bendy’s POV

Over the course of my life I’ve noticed something: Being a hero usually isn't worth the effort. If anything, it's a very good way to get yourself killed. 

I labeled Cuphead a hero when I first met him: someone brave and ethical, but reckless and hopelessly stupid. He is all of these things and also none of them. This was a guy who threw himself at the feet of a horrible demon and still walked out alive. People, I’ve learned, are always far more complicated than you think they are. For example, one of the things I love most about Cuphead is that he is a wonderful mess of contradictions. I’ve seen him beat up a factory owner and help an old lady across the street in the span of one hour. He can curse up a storm and politely ask for change in the same breath. He’s stubborn as a child, but never holds grudges. And he’s always far smarter than he’d have you believe. Every time I think I’ve gotten a good read on Cuphead, he does something that completely destroys my assumptions. 

After the ink demon incident, Cuphead was hired as my full-time bodyguard. Over the next few months, we found he was a pretty nice fit for the job. Piper had been wanting to step down from bodyguarding work anyway, and spend more time with family. So Cup and I were alone together most of the time, intimidating people, collecting money and generally doing business. We were hardly ever out of each others’ sight, and when you spend so much time with someone you’ve got no choice but to like them. Cuphead had a good sense of humor and he was really easy to talk to. We chatted about work and developed inside jokes that made us both giggle like schoolboys. He told me about his brother, and growing up in the orphanage, and I told him stories about the acting business. We talked about our common interest in the new medium of film, and shared our dreams for the future. 

In a word, we became friends. Certainly an unlikely friendship, the mafia boss and his bodyguard, but somehow we were able to strike a balance between the personal and the business. Cup was a terrible bodyguard at first. He was impulsive, loud, and always asking questions at precisely the wrong time. After some trial and error and an awful lot of misadventures, we learned to trust each other, to read each other’s minds and know the other’s intentions. We even developed a sort of silent communication. I only needed to make a subtle gesture and he would spring into action, following my orders without question. It was only later, when we were alone in my office, that Cuphead would start up with me about this bad decision I made or that idiot that I shouldn’t have paid. It was annoying at first, but I humored him anyway. Those arguments ended up going long into the night, with the two of us debating this strategy and arguing the usefulness of that guy. 

Cuphead wasn’t afraid to stand up to me, to be honest with me, and for that I am eternally grateful to him. He is one of the few people I know who would never cower before a mafia boss, let alone an ink demon. He soon took responsibility for giving me the hydrogen peroxide shots I needed every night to keep my ink levels low. Everything he did, he did with the passion of someone convinced that they were really and truly doing the right thing. Most of my guys are good men because I’m paying them. Cuphead was a good man because he simply didn’t want to be anything else. 

Anyhow, I’d better tell you something about how my business works: Toontown’s criminal underworld is run by a syndicate of seven leading bosses, of which I happen to be one. Each of the seven have code names that correspond to the seven deadly sins; mine, for example, is Envy because my operation is one of the smallest. Despite being allied together, us seven bosses absolutely despise each other and are always looking for ways to inch on each others’ territory without starting an outright war. As much as we hate to be allied, we’d probably bring down the whole damn city if a gang war started. 

Late on a cold winter evening, Cuphead and I were in my office, packing up to go home. I had one more meeting to get through before the day was over, but we were happy to get a headstart on getting out. I was pretty sure this particular meeting wouldn’t take long. 

Exactly 2 minutes after the time our meeting was scheduled, my visitor showed up. Tall and dark, the Devil walked in before Alice had even announced his arrival. He liked to get the jump on people that way. He was a demon like me, but had far greater connections to Hell. Oh, he was a piece of work, alright. Also like me, he was one of the seven bosses, code named Greed because of the string of casinos he owned all over the city. Gambling was his thing. Because of his disdain for suits and his feral grin, he was generally called the Devil. As he sauntered in, a giant cigar between his lips, he was followed by his consigliere, a handsome young fellow known as King Dice. Looking at the two of them, you’d never guess who was the actual boss: Dice in his immaculate suit and perfectly waxed mustache looked far more competent. But that would be your mistake. 

The details of that long ago meeting escape me now; I guess it had something to do with drugs or prostitutes or something equally distasteful. The Devil was never quite satisfied with his own business, he was always looking to expand his operations. This time, though, his new expansion plans would be encroaching on my territory. So we had set up this meeting to negotiate all the legal and financial details of his ideas, and how far he was planning to go, and how many men I’d need to lend him, and what cut I’d get, and so on and so forth. As the discussion dragged on, I made sure to pay attention to the men around me: across the desk, the Devil was rambling on passionately, but Dice was leaning back in his chair, looking incredibly bored. He’d probably already heard his boss’s spiel a million times. Beside me, Cuphead was sitting quietly like a good bodyguard, but giving Dice the evil eye for some reason. Perhaps out of jealousy? Did he see something I did not? Cuphead tended to be a pretty good judge of character, so maybe--

The Devil’s voice startled me out of my thoughts, now asking me for my permission to go ahead and start building his new plans on my territory. I gave him the answer I had already prepped hours before: you may, but you only get a specific amount of leeway, anything beyond that and the deal’s void. This was agreeable to the Devil, who grinned toothily and promised I won’t regret it. Out of the corner of my eye, I saw Cuphead seething silently with pent-up frustration. Oh boy. I was in for it when they left. 

The Devil stood up, thanked me lavishly, and politely left the office. King Dice jerked awake and followed him, looking for all the world like a teenager dragged into his parent’s boring house visit. That man belonged on the casino floor, not in this stuffy office with all this talk of contracts and negotiations. As soon as we heard their car racing off, Cuphead lit into me. 

“That was a crap deal, boss, and you know it.” 

He’s never called me “Bendy”, even though I’ve asked him to. He only calls me “boss”, even if I’m not around. I guess it’s supposed to be deferential, but he uses it more like a nickname. 

“From a man who makes his money off craps games I should expect a crap deal,” I joked. 

Cup rolled his eyes and tried not to smile. “I’m serious. His plan is absolutely insane. No one in the syndicate is gonna go for it--there’s no money in it.”

“We don’t know that for sure. You know the stock market’s been a little shaky lately. Who the hell knows where money will come from tomorrow?” 

“I know, but I still don’t like it. I’ve seen that Dice character around; he cheats his customers and gets them to buy him a drink afterward. That’s bad business. So why even bother giving them a little leeway?” 

“Because that’s good business.” I lit up a pair of cigarettes and handed him one. “It shows ‘em that I’m at least interested in what they’ve got to say.” 

“Yeah, and it shows ‘em that they can walk all over you.” He took in an angry inhale. “Give ‘em a little, they’ll just keep taking more and more. You can’t trust these guys.” 

“Believe me, I know. But we gotta be patient and think about the long term. Who knows? Maybe his dumb idea will actually bear fruit.” 

Cuphead didn’t look convinced, but decided not to push it. He evidently had more important things on his mind than arguing with me. Without saying much else, he helped me pack up the office and quickly headed home. 

I probably should have realized, at that point, that something was wrong. Cuphead was clearly preoccupied with something over the next couple of days, although he still did his work as usual. I wanted to ask about it, but didn’t want to be intrusive. Perhaps I should have asked. When Cuphead did tell me what was bothering him, it resulted in our first major fight. 

He came into work one morning, a few days after our meeting, looking like a teapot about to boil over. Whatever had been going on the last few days had obviously reached its climax, and he was not at all pleased about it. As he was locking my office safe, I took the opportunity to ask him. 

“What’s up, Cup?” I nudged his shoulder playfully. “Upset over some spilled milk?” 

Cuphead hesitated and pursed his lips in frustration. He avoided eye contact. 

“Mugman applied to college.” 

“He did? That’s wonderful.” 

I had met Cuphead’s younger brother once or twice before. Nice kid, but a little shy. He appeared to be remarkably intelligent, able to calculate long lists of numbers, and whenever I saw him he had a textbook under his arm. Thanks to Cuphead’s relatively large paycheck, Mugman was able to not only attend school, but excel in it as well. 

Which is why it surprised me when Cuphead said, flatly, “He didn’t get in.” 

“No? That’s too bad, he seems like a good student. Perhaps his grades weren’t good enough.” 

“His grades are amazing,” Cuphead aggressively twisted the safelock as he spoke. “His teacher told me his test results were one of the highest in the class. He didn’t get in because they’ve filled their goddamn quotas for object-heads.” 

“Ah…” I was afraid that was the case. Cuphead worked his whole life to give Mugman a good future, and now society had put yet another stumbling block in his way. Obviously he was thinking the same thing. 

“Those colleges don’t care about good grades,” he grumbled, standing up and examining the safe. “Mug’s as smart as any of the kids they got, but they won’t take him!” 

Cup looked at me now, his voice rising with anger. “Why? Because he looks a certain way? Because of where he comes from? Because of something he can’t even control!? What’s the world coming to when the average kid can’t even get a decent education! To hell with that!!”

And he kicked the safe, making a loud metal clanking sound. I think he might have left a dent.

“Please don’t break anything,” I said, alarmed. “Kicking things isn’t going to get Mugman into that college.” 

“I wish I could kick those stupid admissions people!” Cuphead raged. “Hell, I’ve a mind to go down to that college and give those bastards a damn good reason to let Mug in!!” 

“Don’t be stupid, that’ll just get you arrested,” I argued. “You can’t just go flying in fists first! You’ve gotta be patient and--”

“I can’t afford to be patient!!” he turned on me. “Mugman will have to wait a whole year to apply for college again if he misses this, and we can’t afford that!! He’d have to go back to work again, and all because these idiots have something against kids like him!!” 

“Something else might come along, just wait--” 

“Oh, sure, you’re rich enough to wait! You’ve got men doing literally everything for you anyway! But Mugman’s actually had to work for it! He’s studied harder than anyone!! And being patient just got him screwed over! You always say “be patient” but really, you just let everyone walk all over you! Even the Devil knows he can just walk all over you because of your stupid patience--” 

“Are you telling me how to do my job?! Patience has helped me keep this business running!! Your reckless stupidity is going to get you killed!!” 

That apparently hit a nerve. Cuphead’s face turned very red. “Being reckless is how I’ve survived this long!! Being reckless is what got me this job!! And if you don’t have the guts to act then I’LL DO IT MYSELF!” 

And with that he stalked out of the room and slammed the door behind him. A silence fell over the office, or maybe it was just the silence in my own head. I waited until I heard him slam the front door shut before breathing again. 

I sank into my chair and gave a long, deep exhale. I was surprised by how...unsettled I was. Smushing my stump of a cigarette into the ashtray on my desk, I forced myself to continue my regular paperwork, but all the while I was thinking about him. Of course, Cuphead was not exactly angry with me, he was angry at the racism in his way. And who could blame him? The college’s answer was not just a rejection of Mugman, but also a rejection of everything Cuphead had worked so hard for. The ruthless system that he was now up against was the same one I had been fighting my whole career. The reason I have this power, I reminded myself, was so that I could help people like Cuphead. People who go against the grain of society and find themselves left behind. Most of the guys in my employ, they’re not full time. Most of them have other jobs. But at some point, I did them or their families a favor, and they found a way to pay me back. Often I ask them for nothing but loyalty. And in return, I do everything in my power to get them out of their situation. By the end of the day I had resolved to get Mugman, somehow, into that college. 

The next morning a couple of my guys took the train up to the school in question. They were ably led by Norman Polk, a man notorious for his ability to see in the dark, owing to the fact that he has a projector for a head. I once made the mistake of asking him if he’d seen any good movies lately, and he wouldn’t talk to me directly for a week. Anyhow, I arranged for my guys to meet with the college president and see if they couldn’t talk him into letting Mugman in. Of course I did my research first; Boswell Lotsabucks was an old-money traditionalist who prized his values above everything except his sketchy fundraising schemes. It seemed to me he’d be a tough nut to crack, but I had faith in my boys. So when I got a call from Norman around the middle of the afternoon, I knew it was gonna be interesting. 

“He won’t take the money, boss,” Norman said simply, without so much as a hello. Says it ain’t much higher than regular tuition. And he spouted some nonsense about priorities and the school values and whatnot. Might need to get a bigger bribe.”

“Are you still in his office?” I asked quietly. 

“Yeah, I asked to borrow his telephone. The boys are chatting him up so I could talk to ya.” 

“Put him on the phone, please.” 

There were some disjointed voices as the phone traveled. Next thing I hear was Boswell indignantly shouting something about his rights, and who the hell do I think I am, and how dare I think I can intimidate him like this, and what kinda greedy fool do I take him for, and he’ll have the police on us, and every other little thing. I waited, patiently, for him to quiet down. It’s best, I find, to let a fellow speak his piece before delivering a crushing blow. 

“Mr. Lotsabucks,” I said sweetly, when he had finished. “I don’t want any trouble. But I think we can help each out a little bit. I would really hate to remind Mr. Cagney Carnation of the time you embezzled funds in his employ to finance that new gimnasium you built last year.” 

I heard only furious spluttering on the other end. The threat of fellow mob boss Cagney Carnation ( aptly codenamed Wrath) was an empty one. Cagney can take care of his own business. But it did send a signal to Lotsabucks about who I was and who my allies were, without directly giving out my identity. After a few seconds the phone line went dead. 

Two days later Mugman got an acceptance letter. 

“You sneaky old son of a cockatrice,” Cuphead hissed across the desk at me, barely suppressing a big grin. “You did something. I don’t know what, but you did something.” That acceptance letter had your filthy little fingers all over it.” 

It was the day after Mugman left for school, the first time he had ever been away from home. Cuphead was saddened to see him go, but even their separation couldn’t dampen his joy that day, joy that he hid beneath his usual playful contempt.  
“Is it my fault the school president needed just a little bit of persuasion?” I asked, innocently folding my hands beneath my chin. 

“Don’t tell me! I don’t wanna know what you did,” Cuphead pretended to cover his ears dramatically. “I won’t be an accomplice to this scheme. Mugman already thinks I’m some kinda highway robber.” 

“You told him the truth?” 

“He’s my brother, he won’t tell a soul. Only he made me swear not to hurt any children,” Cuphead chuckled. “And to write to him as often as I can, and not to get myself killed.” 

“The last one might be a little harder to keep,” I said, “if you don’t stop taking all the coffee in the morning. Norman Polk without his caffeine is rather terrifying.” 

We both laughed at the dumb joke, and just like that, we were friends again. Neither of us mentioned the fight from earlier; we didn’t need to. Cuphead had already forgotten and I had already forgiven. 

“Hey, boss?” Cup punched me playfully in the arm. 

“Thanks. For everything.”


	5. The Hero

**Summary for the Chapter:**

> Cuphead plays at being a detective again.

**Notes for the Chapter:**

> Hey ya'll: Please stay safe, have a happy holiday season, and THANK YOU FOR READING!!!
> 
> Chapter warnings: cartoon violence

Cuphead's POV

“Race you to the train station!!” 

I watched Mugman dash up the street, suitcases and all, towards the crowded station. I knew he was just trying to lighten the mood, but getting to that train station was the last thing I wanted to do. Because when we got there, he would leave me. 

Don’t get me wrong, sending Mugman to college was an absolute dream come true. No one had worked harder than he did to get in. All that studying and stress and worry and anxiety had finally paid off. He would get opportunities that I never had, ones that our parents never had. But now that the day had come, and I was going to see him off, my heart felt heavy. We have never, ever been separated before, not since the day we were taken into the orphanage. Mug and I were practically attached. Now we were going to have to let go, and I wasn’t sure I was ready to do that. Of course I was happy that my brother got to go to college, like he always wanted. But I also felt, a little bit, that I was somehow being left behind. 

On the train platform, there were many other people seeing off their loved ones, waving tearfully and shouting at them through the train’s windows. Suddenly both Mugman and I felt rather awkward. Neither of us knew how to say goodbye. We never thought we’d have to. But Mug had to get on that train, so we hugged and Mug promised he would visit on holidays and I promised to write to him at least once a week, if not every day. We didn’t cry, but I saw Mugman brush his face with his sleeve once or twice. 

“Hey,” I said. “If anyone at that school gives you trouble, tell them your big brother will beat them up.” 

“I will,” Mugman smiled weakly. “You’ll be careful, Cuphead, won’t you?”

“Now don’t you go worrying about me. Better focus on your schoolwork,” I straightened his collar. “And leave the worrying to the professionals, alright?” 

We heard the conductor’s whistle, signifying the train’s imminent departure. We hugged again, repeated our promises, said goodbye again. I watched him drag his suitcases aboard as the train’s engine roared to life. I waited, like most of the others, until the train was long gone down the track, a mere speck in the distance. Mugman was on his way, and my heart went with him. 

I turned and walked, rather aimlessly, out of the station. Bendy had given me the day off today, and I had no idea how to spend it now. I couldn’t bear the thought of going home, to an apartment empty of Mugman, so I wandered down the street from the train station, looking for a distraction. Hmm. Maybe I should just go back to work. Alice always has something that needs to be done, and I was getting bored of wandering the same old streets, and--

“Extry, extry! Hey, sir, you wanna buy a pape’? New gamblin’ house opens today!” 

My thoughts were cut off by the shrill yell of a street newsie nearby. Turning a corner, I saw the owner of the voice: a young toon cat, shouting down passerby with headlines. Round his shoulder was a large yellow carpet-bag with a black pattern, and all his unsold newspapers were haphazardly stuffed into it. I didn’t really need a newspaper, but I suddenly felt the urge to buy one from this kid. I had a special fondness for newsies, seeing as Mugman used to be one, and I was feeling sentimental today. 

So I walked over. “What’s all this about a new gambling house, eh?” I asked, pretending to be curious.

“Read all about it right here, mister,” the cat replied, handing me a newspaper. “You won’t believe who the owner is!” 

“Ah, I think I can take a guess.” I tossed the kid a couple cents and scanned the front page. “Yep, I knew it; old King Dice is behind this one.” 

“Yeah, he sure been making a lotta headlines lately,” said the newsie, already scanning the street for his next customer. “What with him building the place right next to the Main Street Train Station and all - that sure pissed off a lotta city officials. Said it ain’t seemly for travelers to see a gamblin’ house right when they come into town!” He laughed. 

“Now that’s kinda strange,” I said slowly, examining the newsprint. “Ain’t no reason to build the place there unless he needed something transported…” 

You might remember from the last chapter that King Dice’s gang had a little deal going with my gang. Bendy told them they could build on our territory, so long as they stay in line and don’t do any illegal activity without letting us know first. I may be a low-level Mafia bodyguard, but I ain’t stupid. Building right next to the train station meant Dice had prime access to anything that might get delivered from out of town, and why would he need that unless--

“Dice’s smuggling something in,” I said aloud. “And it’s not alcohol, because that stuff comes in by boat. It’s something else, something he’s gotta keep secret...why? Seems like something that ought to be investigated.” 

“Gee, mister, you sound like some kinda detective,” the newsie chuckled. “Like on the radio shows!” 

Now that he mentioned it, I did sort of miss my old detective game, when I would go sneaking around the city spying on gangsters. I was aching for that feeling again, that anticipation when I knew I was on the verge of finding out something secret. I was sure there was something going on at King Dice’s new place, and even if there wasn’t, it wouldn’t hurt to check up on them and make sure they’re keeping to the deal. And what if I found something that could be useful to Bendy? The thought made me tremble with excitement. Discovering top-secret information that could help our gang get a lead on the competition? I’d get promoted for sure! 

“Okay, you got me,” I said. “I’m a plainclothes detective investigating King Dice’s criminal activity. You can call me Cuphead.”

That wasn’t exactly a lie, right? 

“My name’s Felix!” The kid bounced excitedly. “You really a detective? Can I come investigate with you? I’m super good at being sneaky! I can help you a lot! And I--”

“Woah, woah, slow down!” I interrupted. “Detective work can be dangerous. I don’t need you getting in trouble.” 

“I know how to get out of trouble,” Felix insisted. “My magic bag can get me out of just about anything.”

“Your magic what now?”

Felix swung around that big yellow bag of his. It was full of bulky newspapers, but he pushed them down into the bag like they were flat as feathers. Then he turned the bag upside down over his head, but no newspapers came falling out. Instead, he shoved the bag down on his head, and you won’t believe it, but that bag swallowed up his head, shoulders and torso without seeming to fill up at all. You could shove a house in that thing and it wouldn’t look like anything but a regular old carpetbag. 

“That’s a neat trick,” I whistled. “You must be real popular at parties.” 

“It is magic,” Felix huffed, pulling himself and the newspapers out as easily as they went in. “And it can carry anything! Pleeeease let me come along and help!” 

Hmm...even if that bag was just some kind of illusory trick, it could still be useful. And I could tell this kid wasn’t going to leave me alone until I said yes. Besides, he could be a witness if I found anything damning, and as a child he can be pliable and easily manipulated if I needed it. So I gave in and told him he can come.

We agreed to meet in front of Dice’s new place later that evening, or whenever Felix sold all his newspapers. A part of me, the more intelligent part, was worried about bringing a kid along. Knowing my luck, we could run into some real danger. But it’s just a scouting job, I argued with myself. We won’t engage or start up anything. We’ll just take a look around, see what we can find, and be on our way. Dice and his goons can’t stop us from just dropping in to check out his casino. It’ll be safe. It’ll be fine. I thought about bringing a gun, but decided against it. I find that gunfire tends to make most problems worse. No, we’ll be fine without it. Felix might be a child, but if that bag of his really is magic, it would be unwise to underestimate him. Magic in Toontown is pretty rare, and usually evil, like Bendy’s demon problem. A magic carpetbag could be plenty useful, no matter who owns it. 

I was surprised when Felix showed up late to our meeting spot. I thought, not without a feeling of relief, that he had chickened out. But nah, he came rushing by in a minute, panting breathlessly, explaining that he had some trouble selling the last few newspapers. But he was still ready and willing to go “detectiving just like Dick Tracy,” as he put it. So without further ado we entered the casino. Since it was already evening, the place was fairly crowded and had a relaxed atmosphere to it. There was a low ceiling and an almost grungy aesthetic, like a seedy old tavern that all the locals hang out at. Craps tables and old-fashioned slot machines were arranged in neat symmetrical rows. Dice was nowhere to be seen, though I did recognize some of his underlings manning the tables. I had definitely gotten into scraps with one or two of them before. Small crowds were formed around the big gambling tables, but most people were milling about between the slot machines and the bar. 

Felix and I got down to our search. When Felix asked me what exactly we were looking for, I realized that I didn’t have an entirely clear idea myself. So I just said to look for anything that might connect this place to the train station. Or whatever looks suspicious. Here’s the real kicker though: we couldn’t find a damn thing. I swear we swept through each and every corner of that building and there were no stairs, no backdoors, not even an “employees only” sign. We examined the slot machines, searched the gambling tables, even talked to the bartender. Absolutely no clues to anything unusual. I was beginning to doubt my instinct that there was something going on here. Felix of course thought the whole thing was great fun, but after we had gone around the lobby for the third time, in case we missed something, even he was getting bored. There was really and truly nothing suspicious about this casino. 

“Hey, Cup?” Felix tugged at the end of my shirt. “I need to go to the bathroom.”

I sighed, taking this as a sign of defeat. I was starting to feel disappointed and honestly, I needed to use the bathroom too. Since there was obviously nothing here and I had embarrassed myself enough in front of the kid, I figured we had better call it a night and go home. Not much use dragging this out. So we crossed to the other side of the casino where the public bathroom was. I did my business and waited for Felix to finish up. As he was washing his hands I leaned my head against the bathroom wall...and heard something deep and hollow. Huh. That’s odd. Solid wall only sounds hollow like that when there’s no structural support behind it. Curious, I turned around and began knocking on the tiles, listening for the noise behind it. The entire wall sounded like there was emptiness behind it. 

Meanwhile, Felix was watching me listen to the bathroom wall like a crazy guy. “Uh...Cuphead? What are you doing?” 

“I think this wall’s hollow,” I explained. “And it just don’t make sense for a bathroom wall to be hollow unless it’s dividing a room. There must be something behind it!” 

“Really?” Felix, catching on, immediately brightened up. “That would make a terrific hiding spot! We just gotta knock down the wall!” 

“No, that’d be too noisy,” I argued. “There’s gotta be a better way to get through this thing without attracting too much attention.” 

“Hmm…” Felix thought for a moment. “Oh! I think I have a hole in my bag.” 

“You have a what?” 

Felix reached into his yellow carpetbag, rummaged around in it, and pulled out a circular black hole. “Yup, I do have a hole in my bag!” 

And without further ado he stuck the hole onto the wall. It made a weird slurping sound as it adhered to the surface. I peeked inside the hole and found a three-dimensional darkness. I had my doubts, but before I could say anything Felix hopped into the hole and was immediately swallowed up by the blackness. 

“Woooah! Cup, you gotta see this!!” he called, his voice echoing like he was in some sort of cave. 

Of course I followed him in. Going through the black hole was like going through outer space for a second, but then we were on the other side of the bathroom wall. As soon as I went through, the hole closed itself up. 

“Oh my god,” I gasped. “We actually did it.”

We found ourselves in a dimly lit tunnel. A rudimentary electrical system ran down the length of it, providing just enough light to see by but not enough to attract much attention. The path in front of us sloped downward, leading somewhere underground. 

“Felix, you’re a genius!!” I whispered happily. “Let’s go!!” 

We headed down into the tunnels beneath the casino. The path wasn’t as long as I thought it would be, but then parts of it still seemed to be under construction. There had definitely been people down here; we saw stray wires and old wooden boards and even a couple hardhats lying around. But there was no one here now, any workers had probably gone home for the night. If the casino had opened recently, of course they wouldn’t have had time to finish building this tunnel. But why was it here? And where--

A deep rumbling interrupted my thoughts. Then it grew louder and reverberated throughout. Suddenly the entire tunnel was shaking. The very ground trembled and bits of dust fell on our heads. The ceiling vibrated so rapidly I was afraid the whole thing would come crashing down on our heads. Felix instinctively clung to me, holding on to my hand so tight it hurt. 

“Is it an earthquake?” he asked, voice high with terror. 

Before I could answer, a high train whistle sounded directly above us. Although the rumbling continued, my mind seemed to clear. Wait a minute. Earthquakes don’t whistle. 

“It’s a train!” I whispered. “We’re underneath the train station!!” 

Aha! I knew something fishy was happening here! Dice had these tunnels built to connect the casino to the train station! That way, whatever he’s smuggling in could be transported quickly and secretly through the tunnels without attracting suspicion! I was practically bouncing with excitement now. Wait till I tell Bendy and the others what I’ve found! This was big! This could be a really big deal! 

"Cup, come look at this!" Felix called from a little up ahead. He seemed even more excited than I was and raced ahead to see what he could find. When I joined him he was examining a neat pile of wooden crates stacked on top of each other; obviously newly arrived cargo waiting to be transported. Felix noticed fresh footsteps all around the boxes, indicating that people had been here recently and would probably come back pretty soon. But what really surprised me was the label printed neatly on each crate: OPIUM. 

Drug smuggling! My heart leapt into my throat. This was big, bigger perhaps than I had bargained for. The opium trade was international, reaching all the way to China and back again. This could possibly go even beyond breaking a treaty between Toontown Mafia gangs. If Dice and the Devil were really in the drug trade...no, don't think about that now. We don't have much time here, need to make our time count while we got it. Thankfully I'd had the foresight to bring a camera; a small kodak Mugman got me for my birthday. I snapped a few photos while Felix kept watch. I got pictures of the boxes and the labels and the tunnel. I was just leaning around the boxes to get a picture of the footprints when I heard Felix shriek. 

I jerked up, hit my head on a crate, and stumbled back. A guy with a giant 8-ball for a head had snuck up on us, his eyes bulging and detached mouth curved into a wide grin. Before we had time to react, the guy screamed in a high pitched voice,

"BOSS! WE GOT COMPANY!" 

Within minutes more thugs from Dice's gang were racing down the path we came on and stepping out from rooms I hadn't even seen. This tunnel system was more extensive than I thought. In no time at all we were surrounded, guns threatening our every move, and King Dice himself stepped forward, smirking at us.

Now, there ain't nothing I love better than a good fight. Calculating in my head, I figured I could probably take down three or four of these losers and trick the rest into fighting among themselves. If I was lucky I could even get away without getting shot at. Either way I knew it wouldn't be too difficult to escape and scramble up the exit tunnel to the station and the street. The only problem with this scenario was Felix. I wasn't sure I could get both of us out, and I sure as hell wasn't gonna leave him. So I sat tight and clutched my camera and watched King Dice. He was spluttering mad to see me.

"So, Bendy's got his stooge spying on us now?" Dice demanded. 

"I'm workin' alone," I retorted. "Have you gone crazy, Dice? Your drug smuggling is gonna put the whole syndicate in danger! If this gets out, it'll lead to a gang war!"

"That's why it ain't getting out, stupid," Dice said smugly. "I dunno how you got in here, but you ain't getting out either. How's our drug smuggling any worse than the whiskey bootlegging you and your boys get up to?" 

"Bootlegging?" Felix's voice became very cold as he turned towards me. "You're one of them? You told me you were a detective! You lied to me!" 

He looked so hurt that I turned away, unable to meet his eyes. 

"It doesn't matter, anyway. You're too late," I said to King Dice. "We already got photographic evidence." I gripped my camera tighter.

"When the police see those pictures, you're finished," Felix added, his voice cold as ice and strangely adultlike. 

Dice gave the kid an ugly grimace. "And just who the hell are you supposed to be?" 

Felix didn't answer, just stared stonily.

"Wait a second, I recognize you," one of Dice's thugs, a cigar-shaped man, wheezed at Felix. "You're dat newsie who's got a beat by the central police station! This kid," he added to Dice, "spreads fake news and digs up dirt for the cops!" 

"You're a police spy?!" I whirled on Felix. Now it was his turn to look guilty, glancing at the ground.

"W-Well, you're a mafia spy!" he protested.

"I don't care what you are," Dice roared. "GIVE ME THAT CAMERA!" 

He launched himself at me, hands reaching to snatch my kodak. I dodged him, only to spin towards two more guys ready to pummel me. Looks like I had a good old-fashioned fight on my hands! 

Fists went flying and legs went kicking, and I was having a grand old time playing keep-away with the camera. But things started to go south when the big jerks realized they could attack Felix without getting hit back. Technically, I could force my way through and make a strategic escape with the camera. That's what Bendy would have done. I remember what he told me when we first met: A real gangster doesn't get himself in trouble. But I glanced at Felix, dodging punches and hissing wildly. A real man doesn't leave behind a partner. 

I launched myself into the chaos, knowing full well I was losing strength, knowing full well there were really too many of them for me to take down by myself.

"Felix, go long!!" I hollered, and as he broke free from the fight I summoned all my old baseball pitches and threw the camera. Miraculously, it bounced off the wall above him and landed in his hands almost undamaged.

"GET THAT CAMERA!" Dice shrieked maniacally, and two thugs raced forward. Felix's rapid feline reflexes allowed him to just barely slip from their grasp and scramble, practically on all fours, down the exit path towards the train station, camera in hand. The two thugs followed him. 

I continued to fight as long as I could, but now all their attention was focused on me. My vision became a blur of bodies. Somewhere beyond the chaos I heard Dice's voice. He was outraged and more than happy to take his fury out on me. I felt two swift punches to the gut, both of which took every bit of air out of me. Another blow to my head scrambled my brains and made everything blurry and unfocused. There was other pain too, other explosions in my nervous system that made my body white-hot with agony. I don't remember those much, though. I didn't remember much of anything after that. 

As a matter of fact, I was pretty sure I was dead. Pretty sure after Dice and his boys had their fun, they put a bullet in my head and that was the end of that. It's what Bendy and I would have done. I'm no victim deserving of pity. Just a washed-up bodyguard who was in a little over his head. That's why it was surprising when I gradually came to the realization that I wasn't dead. It took a while though. My consciousness swam before me, fading in and out. Sometimes I was aware of voices, people around me. Most of the time I was dead to the world. When I was semi-conscious, I thought of Felix. God, I hope he made it. Even though he was a spy, even though he manipulated me into helping him get info for the cops. I wasn't exactly honest with him either, so I guess we were even. At some point I felt something soft under me, a bed or blanket. I saw light behind my eyelids. 

When I did finally come to my senses, I kinda wished I stayed unconscious. My chest felt like it had been trampled on by elephants (two broken ribs) and my right arm hung uselessly (broken in three places) by my side. Not to mention all the bruises and cracks. Any kind of movement was pretty much just pain. Eventually I realized that the soft stuff beneath me was a bed and the light coming in was from the sun and all the people around me were nurses. I had absolutely no memory of ending up in a hospital, but the nurses and doctors were awfully nice about it all. They fixed me up real good and took care of me all the time I was in the hospital recovering. 

Two days after I woke up, a bunch of my mafia friends visited me in the hospital. Gosh, but I was happy to see friendly, familiar faces again. I was also relieved when they assured me that Mugman didn't know anything about what happened; he was up in college and didn't need to be worrying about me. The guys talked and joked with me as usual, saying I had guts and didn't I give old Dice a run for his money! Haha! Awfully lucky that the cops found me when they did, and brought me to the hospital when they did. But they didn't mention anything about the drugs or the tunnels, and I didn't ask. Probably still being kept under wraps. I didn't ask about Felix either, though I was desperate to know if he was okay. I didn't wanna get his name involved in all this, if it wasn't already. 

Later that evening, Alice Angel, Bendy's secretary, showed up. Not to visit me, of course, but to lecture me. How dare I go off by myself like that, and didn't I have any kinda survival instinct, and how could I put myself in danger without any regard to anyone else, and how I'm lucky to be alive and if Dice had shot me I may as well have deserved it for running off like an idiot. And on and on she went, listing off the consequences of my actions and if I ever pulled something like this again I was finished, for good. That's Alice's tough love for you. Unfortunately, I was hopped up on pain meds when she was giving this lecture and too high to really process what she was saying, let alone respond. 

I dreaded seeing Bendy. Alice was right, as she usually is, that I had stuck my nose in too far this time. He must be real pissed at me. The funny thing about Bendy is, his bark is worse than his bite. He can be really petty, losing his temper over the smallest things and making everyone's lives miserable. But when it's something big, when it threatens his business interests, he gets real cold and real quiet. That's the kinda anger that gets people killed, that makes things happen. The anger that the demon feeds off of. This time I nearly got myself killed, but next time I could really endanger the buisness, and that was something Bendy couldn't tolerate. I guessed that was why he didn't visit me right away; he was angry at me. But Bendy loves being unpredictable, so I suppose I shouldn't have been too surprised that, when he did visit the next day, it was with his usual customary grin. 

"How's my hero feeling today?" He asked mockingly, taking advantage of my weakened state to pinch my cheek, which he knows I hate but does anyway. 

"Hero?" I repeated warily. "What do you mean?" 

"See for yourself," he handed me that morning's newspaper. With my good arm I held it up close to my face. 

Beneath the headline 'DICE DRUG RING BUSTED', an article stated that, thanks to an anonymous tip, police had investigated an extensive tunnel system connecting Dice's casino to the train station and beyond. They had followed the trail down and discovered a wider drug traffic ring. Although Dice and his thugs had escaped, many drug dealers were arrested. Accompanying the article was a photograph of the opium crates. A photograph that I had taken.

Anonymous tip, I repeated to myself. Relief washed over me. Felix was alive. He got out okay. He brought the camera to the cops. They went down into the tunnels and found me, probably left for dead by Dice. Felix saved my life, even though I had lied to him. He probably never wanted to see me again, but right now I thanked God he was okay. I told Bendy the whole story; how I met Felix and our adventure down in the tunnels. How we both lied to each other. Bendy listened in that wonderfully patient way he has, smiling at all the joyful parts and frowning seriously at the scary ones.

"I only wish," I told him, "that Felix and I could have been friends." 

"Well, that would explain this letter." Bendy took out of his vest pocket a small white envelope. "Someone slipped this under your room door last night. Nurses didn't know what it was, so they sent it to me. I was gonna give it to you today anyhow." 

Inside the envelope was a scrap of paper. Written on it, in a messy and childish hand, were exactly five words and beneath that, a local phone number. The note read: 

Thanx for th adventur  
Felix


	6. Intimacy

**Summary for the Chapter:**

> Bendy spends an entire chapter trying to figure out his feelings for his bodyguard.

**Notes for the Chapter:**

> Basically the internal monologue of a bisexual disaster, plus more character development for Alice! 
> 
> Can't believe it took me five whole chapters to get to the actual shippy part of the fic lol Anyhow, thanks for reading yo <3 May you be blessed with a happier new year.
> 
> Chapter warnings: Mildly sexual content, brief description of rape

Bendy's POV

After Cuphead's adventure under Dice's casino, I started calling him a 'hero'. 

At first it was supposed to be sarcastic, a snarky insult for when he was being too nice or too reckless or too loud. But slowly, over time, the nickname transformed into a sort of...term of endearment. Like many of the jokes we made, my calling Cuphead a hero became an inside message, a code word for "You're being an idiot and I kinda love that." He of course had a few nicknames for me too, like 'devil darling' and, ironically, 'angel'. Most of the time though, he just called me boss. It was a long while before he felt comfortable calling me Bendy. The closest he came to that was 'Ben', and once, when he was in a peculiarly playful mood, 'Bendles.' All this is to say that though we maintained the same professional relationship we always had, our language was evolving into something more, and neither of us were prepared for it. 

Cuphead was right, by the way, about why I didn't visit him at the hospital right away. Well, partly right. I was furious at him for doing mafia business by himself, without telling us, putting himself and our interests in danger. But it wouldn't do any good to get angry at him when the deed was already done, especially after Alice had already yelled at him about it. But something else about that incident upset me as well, something that I did not tell Cuphead about for a very long time. Years later, it's just kind of embarrassing. One of my contacts at the police station happened to overhear that newsie, Felix, when he came rushing in with a camera and a wild story about tunnels beneath a casino. My contact related the story to me soon afterward. When he described how Cuphead threw himself into the hands of the enemy so Felix could escape, I felt a strange jealousy, a possessive anger that was hard to articulate. How dare he throw himself away for someone else, I had thought furiously. His services belong to ME! How dare he throw them away so easily. He knows I have no use for a dead bodyguard! These thoughts, irrational as they are, scared me at first. My bodyguard is a paid employee, not someone I can simply 'use'. Even so I felt upset, somehow, that he was willing to sacrifice himself for someone that wasn't me. Does that make sense? I don't know. Desire, it seems, comes in many forms and is usually irrational. Cuphead has a strong will of his own and moreover, a life outside of work. A life which I am not a part of. I didn’t want Cuphead to see these thoughts in me. Like all inconvenient feelings, I shoved them away and forgot about them. A fearsome demon must be dignified and respectful at all times, a mob boss even more so. My personal, selfish desires would have to wait. 

In any case, I think the adventure under the casino humbled Cuphead a little. He was a little less reckless after that, a little less stubborn about following orders. More mature, even. I just wish he didn't have to get beaten up so badly before that maturity finally settled in. The poor guy's right arm was practically useless for months afterward. Even he admitted to me, privately, that he was only alive because of pure dumb luck. And lying there for weeks in that hospital bed, both Cuphead and I seemed to sense that his luck was beginning to run out. 

One evening, about a week into Cuphead's hospital stay, I was sitting with him and we were chatting like we usually do. Then a nurse came in with more visitors: Alice, her cheeks pink from the cold outside, and Boris, who had escorted her here from work. Hm. Boris sure has been escorting Alice a lot lately. I wondered briefly if he was courting her. I'd have to ask him later. It could be a problem; love does not usually turn out well in the mafia. Anyhow, I introduced Cup and Boris and they immediately struck up a conversation about something or other. I didn't hear much before Alice gently touched my shoulder. 

"I need to speak with you, Bendy," she said in a voice that demanded obedience. "Privately." 

We waved goodbye to Boris and Cup and walked out of the hospital room, to the hallway. It was pretty quiet out here, except for the occasional nurse whizzing by.

"What's on your mind?" I asked pleasantly. "And why can't it wait till tomorrow?"

"I just wanted to thank you for NOT telling me that we're footing this hospital bill!" She hissed. "This is going to cost us, Bendy!" 

"Don't we give health insurance? Okay, look," I added hastily as she gave me an evil look. "It's the least we could do after he nearly got beat to death, and it's not like he has the money to pay for it himself!”

"I know you have to help our guys, but you're going to help us straight into bankruptcy! We're not made of dough!" She sighed heavily, pressing her fingers to the bridge of her nose. "Besides...don't you think you're helping Cuphead a bit too much? I mean, this is the second time this week you're visiting him. Do you like him?" 

I was so startled by this abruptly personal question that an answer spilled out of my mouth without even thinking about it.

"Of course not. Cuphead is a liability and it's strategically important to have an eye on him at all times. I'm just trying to cultivate him into being a valuable gang member. The friendship is just a front to gain his trust.” 

Even as I said the words I realized how wrong they were. Even if there was a little truth to them, my feelings for Cuphead had long since surpassed any business strategy. But Alice just smiled. 

"You don't have to act all macho around me, you know. I don't really care what you do after work. Just let me know when you're making financial decisions, okay?" 

I nodded, and she patted my shoulder, her eyes softening. 

"Hey, we haven't had you over for dinner in a little while. Why don't you come over tonight? It'll be nice." 

I blinked, distracted. "Hm? Oh, yeah, of course. I'd love to come over. Seven alright?" 

We headed out the door together and parted ways. I watched her disappear down the street and exhaled deeply. My head hurt. Why in the name of hell did I lie to her? Why did I feel the need to hide my friendship with Cuphead? It's not something I should feel so defensive about. I'm used to lying, but I wasn't even sure why I had lied to her, and that bothered me. Self-doubt is not something I'm used to. A good leader never doubts himself. Damn, I need a smoke. All this recent stress has been getting to me. That must be it. 

Still the question nagged at me even as I got in my car and lit up a cigarette, watching the city speed by as I headed home. Being friends with Cuphead was nothing to be ashamed of, nothing that needed to be hidden. But the way Alice phrased her question implied that we might somehow be more than friends. Which, honestly, had more truth to it than I really wanted to admit. As I said, love does not turn out well in the mafia. I had lied to Alice because I was really lying to myself. 

Do I like Cuphead? I don't know. I haven't had much experience with liking anyone. Not in that way. When Boris and I played gigs in the Toontown clubs, we always hung around the bar after our act, drinking and flirting with the bargirls and waitresses. Sometimes we went home with them. Those were fun, casual flings, harmless and meaningless. There was no intimacy there, just a couple of young people having fun, exploring, touching each other cautiously. I have fond memories of those girls and the times I spent with them. 

The first man I ever slept with was a jazz clarinetist I met at one of the local clubs. He was an older guy, happy to take a newbie under his wing. Back then I was young and naive, ready to explore new things in a new city. I never told Boris that I was seeing a man; I guess I didn’t want him to judge me. Maybe I should’ve told him. One night my clarinetist took me to a gay bar, where local homosexual men hung out. I remember being surprised at how perfectly ordinary the place was, just some guys drinking, talking, laughing. Occasionally a man in woman’s clothes would get up on a makeshift stage and crack a joke or two, but otherwise it seemed like any other bar in the city. That’s why it was so startling when the police raided that night. About five or six officers stormed in, demanding that everyone line up for arrest. Terrified of being arrested in a city I didn’t know, I ducked behind the bar counter and hid there, listening to the heavy footsteps as the other bar patrons, including my clarinetist, were herded away to the police van outside. For a minute I thought the police might actually miss me, but then a cop’s face popped up above me, leaning over the counter. 

“Hello,” he said. “You’re one of them, aren’t you?” 

It was an observation, not a question, so I didn’t say anything. I didn’t dare move. 

“You don’t have to go to jail,” he continued, stepping closer. “I can get you out, if you want.” 

“How?” I asked suspiciously. 

“How indeed.” He unzipped his pants, exposing himself. 

Five minutes later I stumbled out of the empty bar, rushing past the police without looking up. I didn’t know where I was going, I just wanted to get as far away from there as possible. Finally, I reached a deserted corner and violently threw up on the street. I leaned against the wall, heaving, trying desperately to get the taste of that cop out of my mouth. To this day even the thought of receiving or giving a blowjob makes me nauseous. 

More than anger or fear, I felt a deep disgust. Disgusted with the cop, of course, but mostly disgusted with myself for letting him do that to me. For not rejecting him and just going to jail like a man.I would never ever let anyone take advantage of me like that again. Never. From then on I would always be in a position of power. I would hurt other people so they wouldn’t hurt me. I never saw that cop again. Never saw my clarinetist again, either. After that night, my affairs with men were discreet, a tangled mess of bodies in a dark, deserted alley. Usually, it was just easier to stay with women. 

In the world of organized crime, sex is really just a show of power. Sex has to be a strength, because otherwise it’s a weakness, and weakness is not tolerated in the mafia. It’s pretty common for gangsters to show off their prowess by boasting about how many women they’ve laid or how many mistresses they have. My old mentor, Mister Joey Drew, never liked that stuff. He believed a person’s love life was their own business and shouldn’t be aired out for everyone to hear. He himself had a wife who lived uptown, I think, but they were estranged and never saw each other if they could help it. I don’t remember if they ever got officially divorced. Joey had several girlfriends anyway. As for me, I always hated sleeping with people who only did so because they wanted something from me. Women who wanted their big break, wanted favors, wanted connections with the right people. Some women even wanted to be my mistress or, satan forbid, my wife. I’ve never married. Never found the right person, whatever that means. I guess the only person who’s ever come closest to that was Alice Angel. 

Alice is, without a doubt, one of the strongest people I know. When I first met her, she worked as a bartender downtown near the harbor, handling a broad range of tough characters. She was notorious for keeping her customers in line. It was said that Alice Angel would slap anyone who looked at her funny and that she had fought off two different rape attempts. When Prohibition started, Alice was right out there with the guys, smuggling bottles from the harbor, risking arrest and even her life to keep her little speakeasy going. She was one hell of a woman, and even I stood in awe of her boldness and intelligence. So when Toontown’s criminal syndicate was formed, and the bootlegging became more organized, Alice wasn’t interested in doing the actual smuggling anymore. She quit bartending and, since we were friends by that point, joined my fledgling operation. Officially, she’s my secretary, but really she handles most of the financial issues and helps keep the operation going. I didn’t keep my admiration for her much of a secret, and we ended up dating for almost a year. Most of that year was spent arguing and bickering about everything, from important business decisions to who left the toilet seat up. If I said yes, she had to say no. Our relationship was lively and exhausting, our lovemaking just as passionate as our fights. Eventually our personal fights began to bleed into our work, turning our office into an arena for shouting matches and making everyone else uncomfortable. Something was gonna have to give. In the end we mutually broke up, giving up our personal relationship to save our work one. 

Nowadays I get along with Alice pretty well, and still consider her a good friend. But after we broke it off, I just became too busy for relationships. Too much work to do and not much time to spend on illicit affairs in dark back alleys or strangers’ bedrooms. Is it ever worth the risk? Could I ever love anyone after Alice? Hell, could I even love a man the same way I’ve loved women? I hate questioning myself, doubting myself. But it is true that Cuphead has some of the qualities I would admire in a partner: he’s unfailingly loyal, and kind of smart in his own funny way...and his confidence is absolutely contagious. He has so much faith in everyone around him, it’s hard not to believe in myself when he’s there, challenging me to always do better, be better. Cuphead’s got a great sense of humor, and he’s never afraid to stand up to jerks, and he’s stubborn as all hell, and…

Oh, satan help me. 

As promised, I drove down to Alice’s place at around seven. I really haven’t been over in a while, mostly because, as I said, I’ve just been busy. That and I’ve kind of been trying to avoid her parents. They give me the creeps. Don’t tell her I said that. Alice’s been living with her aging parents, taking care of them for as long as I’ve known her. They’re an interesting pair: her dad is confined to a chair and contents himself with giving everyone dirty looks and barking orders at Alice and his wife in a garbled sort of English. But get him in a good mood and he can tell the most fascinating stories about the old days. Maybe I’m just paranoid, but I think the old man listens and knows a lot more than he lets on. Alice’s mom is good at keeping him in check though when he gets too rowdy. She’s a frail little old lady who shuffles about in slippers all day, tending to her husband and doing everything Alice says. I don’t think the old lady is entirely there, if you know what I mean. Whenever I come over she always seems convinced that I’m trying to sell her something. 

I think at one point Alice’s parents thought I was really gonna marry her, and that’s probably why they don’t like me much. But Alice certainly rules that house, so if she wants to have me over for dinner she most certainly will. They really aren’t that bad, and Alice’s dad really does have good stories. Especially tonight when he was in a particularly good mood because his doctor gave him a new kind of medicine. The old man’s favorite story was how he met his wife, a sweet old tale about new immigrants finding love in a new country. This of course did nothing to distract me from thinking about Cuphead and my own pathetic excuse of a love life. It’s already risky, falling in love, but with a man? What could I possibly be thinking? The whole idea was ridiculous and silly. I don’t even know if he swings that way, or swings any way at all. 

Alice must have noticed how spacey I was during dinner and I guess she attributed it to stress, because she swept through the rest of the meal pretty quickly. At first I thought it was because her parents wanted me out faster. But as soon as the old lady wheeled her husband out, Alice pulled me upstairs to her bedroom. Sat down with me on her bed. Started unbuttoning my shirt. We’d never done it in her parents’ house before, and I think the idea excited her more than anything else. She pulled down my pants, I pulled off her skirt, and things just kinda took off from there. 

I told you our relationship ended a while ago, but sometimes this still happens; we collapse into old habits and into old bodies. I don’t love Alice Angel the way I used to, but her body is safe and familiar. It’s easier to be with her than to think about a risky new relationship. And yet when I closed my eyes, it wasn’t Alice I was lying with. I felt like I was cheating, but on whom I didn’t quite know. Was I betraying Alice by replacing her in my mind? Or was I betraying myself by denying my real desires? 

She hugged me close, her soft curves and familiar flesh enveloping me in their warmth. Alice is really such a good woman, I thought. She deserves to settle down with someone wonderful. Preferably someone more stable than me, someone who will give her everything that I cannot. Because as much as I like Alice...

I am in love with someone else.


	7. Masquerade

**Summary for the Chapter:**

> Chapter warning: Suggestive content

Cuphead’s POV

“Dear Mugman,

Great job on the A in math! You sure gave that professor what for, haha. Really annoying about that classmate of yours, though. If he's still bothering you, tell a professor. There ought to be someone there who deals with stuff like this. Or just tell him your big brother will beat him up. As for me, I'm doing fine…”

I paused. Bendy, sitting beside me and writing down the letter while I dictated, looked up expectantly. Sitting on a hospital bed with a broken arm and busted ribs was absolutely not fine. 

"I hate lying to him," I said finally. 

"Lying is a good skill to have," Bendy remarked, fiddling with his pencil. 

"Yeah, to people you don't like," I frowned. "But this is my brother. We never kept secrets from each other."

"So tell him the truth."

"I can't. If Mug knows I got injured he'll leave school and come back here. I can't let him get mixed up in this criminal business. It's too dangerous. He deserves better." 

"Sometimes lying is the kindest thing you can do." 

"I know, but that doesn't mean I like it." 

"That's your problem, Cup," Bendy grinned, trying to cheer me up. "You're too honest."

"And you're too secretive," I replied. "I can never tell what you're thinking."

"That means I'm doing a good job." 

"What d'you mean?" 

“Hmm, how to explain it…” Bendy thought for a moment, tapping his chin. “You know...lying is sort of like acting. All it takes is a little confidence. If you act like a mob boss, and do it with conviction, people will believe that's what you are. Lying is similar to that. It's like putting on a mask." 

"But even actors have to take off the mask sometimes." 

"Sometimes." He checked his watch. "Now let's finish up this letter, I got a meeting in half an hour." 

While I was recovering in the hospital, I had a lot of time to think. I'm more of a 'do first, think later' kinda guy, so this was pretty new to me. Those were long, lonely weeks, with nothing to do but think. Most of the time I was bored out of my mind. I probably would have gone crazy if it wasn't for Mugman's letters. He wrote dutifully every week, in that curvy handwriting that I can recognize from miles away. He told me everything about his classes and roommates, even things that didn't seem so important but he knew I'd want to know. Each and every one of his letters were treasured and kept under my pillow. I was sure he was doing the same with my letters (which were dictated by me to Bendy or a nurse since I couldn't write well). The biggest highlights of my week were Bendy's visits. He came punctually, twice a week, on Tuesdays and Wednesdays. Maybe it was because I was bedridden, but I felt I was enjoying his company more and more every day. I eagerly anticipated his visits, even convinced the nurses to let him stay a little past visiting hours. When he left, I was bored and lonely again. When something interesting happened, I wondered how I would tell him about it. When I thought of a good joke, I wondered if he would laugh at it. I liked his laugh. 

I thought a lot about what he said earlier, about lying being like putting on a mask. Bendy used to be an actor, so he loves those theater metaphors. But the more I thought about it, the more his analogy bothered me. Telling one lie will always lead to telling another lie, and another, until you’re buried in them, like wearing too many masks at once. At some point you can’t tell where your face ends and the mask begins. Was being a bigshot crime lord really so easy as putting on a mask and playing pretend? If so, what else was just pretend? Was our friendship just a lie too, a mask that he put on whenever he was around me? I didn’t want to believe that, but it nagged at me. Even actors have to take off their mask sometimes. Did Bendy ever take off his? Who was he when he stopped playing pretend? Who was he without the mask? Bendy was my closest friend, but sometimes I felt like I didn’t know him at all. 

Maybe it was that sense of mystery that drew me to Bendy. I don't know. I've never been able to say exactly what I like about him. Words aren't really my strong suit. For that matter, I'm still not sure when exactly I fell in love with him. It was a long and slow process, ultimately resulting in the gradual realization that I've actually loved Bendy for a very long time. 

This whole love business was new to me. I had practically no experience with relationships. Mostly because I was just plain busy; when I wasn't working, I played detective or hung out with the guys or spent time with Mugman. Then I had absolutely no interest in women; not in that way, anyhow. Sure, some women are very nice-looking. Alice Angel is very nice-looking. But I just didn't see the point in a guy making a complete fool of himself over a woman. It didn't seem important to me. Sometimes I thought about getting married and having kids, but that was always in the distant future. For now, Mugman was enough family for me. Before I met Bendy, the idea of being with a man, let alone with my boss, was simply unthinkable. Then again, I've done a lot of unthinkable things lately. I faced off with a demon, busted a drug ring, and nearly died at least twice. After all that, being with Bendy didn't feel so impossible. 

I was released from the hospital, finally, feeling almost as good as new, except for my arm, which still needed some rest before it'd be fully healed. Most of my other injuries had long since faded away. I practically ran all the way home from the hospital, eager to call Bendy and get back to work. After so many weeks of boredom, I was just aching for some action. A new job would be just the thing to distract me from those nagging thoughts about love and masks and complicated feelings. Unfortunately, Bendy's new job was not at all what I had in mind. 

"Some city official hotshot is throwing a big charity ball, and everybody who’s anybody has gotta be there to kiss his ass," Bendy explained over the phone. "Including the other syndicate leaders, and they’re definitely bringing their own security. I’m gonna need you there to play bodyguard.” 

Charity ball? Sounds like a big party for rich people. Bleh. I've never been fond of parties. Mugman used to get anxious around crowds, so we tended to avoid them. I'd much rather get a beer with some friends and hang out in some cozy old bar. Besides, I was not particularly eager to see gang rivals so soon after getting out of the hospital. 

"The doc said no fighting and no dangerous jobs till my arm’s fully healed," I informed Bendy.

"How could it be dangerous? Nobody would dare try anything, not at a big party with hundreds of people.”

"Sounds pretty dangerous to me."

"All you have to do is show up and look tough, okay? No fighting, no gang stuff. We’re just there to represent our business interests. Understand?” 

"Okay, okay, I got it."

"Oh, and Cuphead?"

"Yeah, boss?" 

"Make sure you wear a suit." 

I had to dip into my savings a little to get the suit, but as it turned out, getting it all fit and tailored was worth it. Hey, if I had to wear a fancy monkey suit, at least it was comfortable. Generally I don’t give a lick about my appearence, but even I had to admit I looked pretty darn good in that suit. Even the tailor said it fit like a glove. But none of that compared to Bendy’s face when he saw me wearing it, the night before the charity ball. 

“Damn,” he breathed, looking me up and down. “You look swell, Cup.” 

“You don’t look bad yourself,” I chuckled, but before I could finish the sentence Bendy stepped towards me suddenly, reached out and began fiddling with my collar, the way a wife fixes up her husband before he goes to work. The gesture was so sudden and intimate I nearly stepped back in surprise. Luckily I managed to stay still and just let him do it. 

“There, now it’s perfect,” Bendy stepped back, looking at my suit admiringly. Or was he looking at me? No, don’t be stupid! 

“We’re going to a party. You should relax,” Bendy smiled. “After everything we’ve done recently, we deserve a break, right?”

I nodded tightly, feeling anything but relaxed. There’s no point in applying meaning where meaning doesn’t exist. It was just a friendly gesture, that’s all. Yeah. Friendly. Focus, Cuphead! Even though it’s a party, I’m still on duty and should remain alert. No getting distracted. I wish Bendy’s smile wasn’t so painfully distracting. 

The charity ball took place in the ballroom of one of the fanciest joints in Toontown, the Hotel Natwick. Strictly one-percent only, it was the kind of place where you’d find poor kids, myself included, peeking longingly into the windows, trying to catch a glimpse of some celebrity or whatever. I could hardly believe I was actually going inside. Of course Bendy strode in like he owned the place, but even he shielded his eyes from the intense brightness that greeted us. The sheer opulence of the ballroom was overwhelming. Giant stained glass windows, massive chandeliers covered in diamonds and gold, long curtains of velvet and silk, gorgeous clusters of gems on the walls that didn’t even have a functional purpose, they were just there to look pretty. And that was just the building itself. The guests inside were even more beautiful. Long-haired women, wearing dresses in every shape, size and color, their high heels sounding like thunder on the floor of the huge, echoing ballroom. The men wore exquisitely cut tuxedos that put my suit to shame, and their coattails practically brushed the floor, as was the fashion in those days. A hundred waiters in black and white uniforms weaved in and out of the crowd, catering to everyone’s needs. There was so much hair gel and hair powder, the whole room stank like an opera singer’s dressing room. 

Now, I’m no wallflower. I know how to be the life of a party. And in any other circumstances, I would’ve happily rubbed elbows with these rich and famous fatcats. But as I watched Bendy blend into the crowd, mingle and converse like he was right at home, I felt a crushing sense that I was way out of my league. Bendy knew all these glamorous people, these attractive women, these charming men. He could have anyone he chooses, anyone with money and looks and charm and maybe, if he’s lucky, even a personality. With all these options so easily grasped, why on earth would he ever be with someone like me, a washed-up bodyguard still struggling to pay his brother’s tuition? Why would he pick me? Hell, I wouldn’t even pick me. I had no chance of being with Bendy. 

With my mood so miserable, I didn’t have the energy to do more than follow Bendy around as he socialized. As a bodyguard, not a guest, I was supposed to be invisible anyway. I fell into my old habit of people-watching, observing the many little behaviors and quirks all people do, imagining that I can deduce information about them. Most interesting of all were our rival mafia members; being polite seemed, for most of them, an excruciatingly humiliating task, but one they needed to perform at such a social event. I could only imagine how they would behave if this wasn’t mixed company. I also noted, with more than a little satisfaction, that King Dice was nowhere to be seen. But mostly I watched Bendy. His body language, his small but significant quirks. The way he forced a smile at bad jokes. How much of it was genuine? Behind closed doors he cursed these people out, calling them bootlickers and robber barons and all kinds of names that I can't put in print. But here at the party, it's like they're his best friends. Which is the truth? What does he really feel? Why can't he ever be consistent? The question nagged at me again: when, if ever, does he take off the mask? 

A suave, smooth-talking man--the host, I guess-- announced that it was time for the main entertainment. All the guests were soon seated at dozens of small circular tables, all of them facing a huge stage with an elaborate screen curtain. I realized then that I had no idea what this entertainment was supposed to be, although everyone around me was whispering excitedly. I was about to lean over our table and ask Bendy about it, but before I could a stressed-looking guy--staff, by the looks of his clothes-- came over and whispered something into Bendy's ear. 

The guy had hardly finished speaking before Bendy stood up. "One of the performers is an old friend of mine, and is having trouble backstage," he informed me. "They think maybe I can help out."

"Should I--?" I began. 

"No, you stay here. The stage isn't too far from here, and I'm sure backstage is crowded enough as it is. I'll be right back, okay?" 

He patted my shoulder, let his hand linger there for a moment longer than necessary. Maybe I was just imagining it. Either way, I watched him disappear backstage with growing discomfort. Now I felt more alone and nervous than ever, the only ordinary guy among all these glamorous people. I watched the backstage entrance anxiously, wishing he'd come back soon. But then the ballroom's lights dimmed, the whispering quieted, and Bendy still hadn't returned. This worried me; I wouldn't be able to find him in the dark. I was about to stand up and head after him when the band started up a funky jazz tune, the curtains drew back and the stage was lit up with a burst of explosive light, immediately turning my attention to it. The show had begun. 

A lone woman strutted onto the stage, confident and glamorous, her features glowing like an angel in front of the stage lights. For a minute, I was rooted to the spot, dazzled by the spectacle. Then I squinted into the light, straining to see her better. I saw a very familiar face. 

Bendy?! 

It was a woman, but not with the features of a woman. He--it undeniably was a he--wore a shimmering dress, tight and slimming on a figure that I'd only ever seen in business suits. There was no makeup, but by the stage lights I could see soft contours highlighting his feminine face. Oh my gosh. Bendy, the mafia boss, was dressed in drag. He sauntered forward, stepping to the beat of the jazz music. He winked at the audience, as though he was sharing a secret, and then began to sing. His voice, deep and unmistakably male, echoed throughout the ballroom. People began to laugh, and I guess that was part of the joke, hearing so masculine a voice out of such a seemingly feminine person. It was an incredibly bizarre experience.

And yet. Bendy's voice was beautiful. Because as I sat there, in that hotel that I had no business being in, among people that I didn't fit in with, everything suddenly became clear. This was Bendy without the mask, without the pressures of playing mob boss. On the stage, he could truly be himself, could be a misfit and an outsider without being judged. He always had charisma, but his stage presence was electrifying, powerful. Dressed in women's clothes, in front of hundreds of people, he put his personality on display for all of them, without shame or fear. Then I understood. Bendy wanted me to see this, his true self, without any mask or pretending. Because he trusted me to hold his mask for him, to see him when he was giving and not taking. Our entire careers revolved around taking and cheating and more taking. But on that stage, there was an almost radiant joy in giving of himself to the audience. And to me.

Haha. I don't know if all that made sense. I just know that seeing my boss in drag was crazy and I think I had a revelation, a sense of clarity. I had been so anxious about being an outsider or not being rich, but really I was worried about not being good enough for him. But I didn't need to. Because a mafia boss dressing in drag is just about the ridiculous thing I can think of. But Bendy did it and he did it with pride and it just made me love him all the more. Kinda funny that Bendy has to act like someone else in order to be himself. Mugman would call that a paradox. I call it typical Bendy logic, so infuriating and so wonderful all at the same time. 

Later I would learn that Bendy's friend, who was supposed to perform that night, became sick right before the show and asked Bendy to take his place. Later I would learn that Bendy actually did this a lot; a little side hobby, he called it, performing drag in various venues all over town, when he wasn't busy with his day job. He always did love acting and couldn't truly leave the stage. Later I would learn that when Bendy was in drag, he was called Bianca. It was a stress reliever for him, to get up on stage and be as silly and dramatic as he liked. To be someone else for once, or maybe to be himself. In the end they mean the same thing, I think. I learned all this later, when I had time to process everything. I don't remember too much else from that night. After the performance, the charity ball descended into chaos. 

There was dancing, food and booze, hundreds of bodies packed together like sardines. To me, everything was fuzzy; a blur of faces, colors and light-- and I didn't even drink. I think I was driving that night. Or maybe I just didn't feel like getting drunk. I don't remember. There's only one memory of that night that sticks out pretty distinctly in my mind. Bendy went and got himself pretty drunk, surrounded by rowdy friends and plenty of drink. He was back in shirtsleeves, but makeup was still smeared across his face. Bendy once told me that demons are funny about alcohol, it doesn't quite affect them like it does to other people. When Bendy got drunk, he got real quiet, as if withdrawing into himself. He swayed back and forth, giggling to himself, before finally falling on me, burying his face in my chest. 

“Heeeeey, Cup,” he hiccuped, slurring his words. “Aren’ I preeeetty?”

I rolled my eyes and pushed him upright. As he moved away from me, he left ink stains on my brand new suit. Ah. That’s probably not good. I knew enough about Bendy’s demon problem to know that dripping ink is never a good sign. 

“C’mon, let’s get some fresh air,” I said, a bit alarmed. “Should at least get you away from the crowd…” 

He didn’t resist as I looped my arm under his shoulder and half-carried him outside, to a little outdoor space behind the hotel. There were benches and street lamps here, but the night air was too cold for anyone to be out here. I figured the cold would make Bendy sober up a little, at least until he could get better control of his ink. Of course I did notice this was the closest we’d been to each other all night. He seemed to notice it too, because he started nuzzling, rubbing his face against my shoulder like a cat. 

“Quit it, boss,” I said sternly. “You’re so drunk, you dunno what you’re doing.” 

I led him over to one of the benches. He twisted out of my grip and sat down first, reaching a hand out to me. 

“M’only a little tipsy,” he admitted, grinning goofily. “But I know ‘zactly what I’m doing.” 

I hesitated, uncertain. His eyes were as clear as the night sky. When I took his hand, he pulled me close, his other hand sneaking around my back, our faces inches apart. I smelled the alcohol on his breath. And then Bendy’s mouth was on mine. Startled, I bit his lip by accident, but he only pulled me closer, fighting me. We pushed and pulled like two magnets with opposite forces. His tongue slipped into my mouth. I tasted ink. Now we were both gripping each other, either because of the cold or because we never wanted to let go. When we did pull away, finally, only a thin mixture of ink and saliva kept us connected. Bendy’s hands, the sneaky little things, were playing with the zipper of my pants. A rush of cool wind on my naked skin brought me back to my senses. 

“No,” I said quietly, looking Bendy in the eye so he’d know I was serious. “I don’t want to, yet.” 

Bendy stared at me. This was a guy who was used to getting what he wanted. If he wasn’t given what he wanted, he took it, by force or by cunning or whatever else he had at his disposal. I’m sure he very well could have taken what he wanted from me, that night, and for a moment I was sure that he would. So it kinda surprised me when Bendy zipped up my pants again and released me from his grip. He seemed forlorn now, the sexual aggression of a moment ago had vanished. Instead he stood up, following my lead, as we began walking back to the ballroom. His hand slipped into mine.

“Hey, boss...is this what love feels like?” I asked. 

He thought for a moment. “I dunno.” 

“Okay.” 

Hand in hand, we walked back into the party, into the world.

**Notes for the Chapter:**

> Oh my god I never thought I'd reach this point. I have never followed up on a long term project like this before, let alone written seven chapters of fanfiction!! THANK YOU SO MUCH to everyone who has read this far!! Every single hit this fic got has extended my lifespan. I could have never done this without ya'll. Thank you. 
> 
> That being said, I'm taking a little hiatus from this fic. Now that the foundational ship has been established, I can take a few steps back and figure out how I want to expand this story from here. I have more ideas for the story and more characters to introduce, but I need time to develop them and figure out how to get to the ending. Believe it or not, there is an ending of sorts to Ben and Cup's story-- two of them, actually. It's complicated. Anyway, thank you all again for following this wacky little journey with me. This story has been years in the making and I'm beyond grateful that I've had the chance to write it out. Thank you.


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